Herbicidal heteroaryl substituted anilides

ABSTRACT

Compounds of formula (D having herbicidal utility are disclosed; ##STR1## wherein Q is a variety of heteroaromatic groups; X is a single bond; O; S; or NR 4  ; R 1  is C 1  -C 5  alkyl optionally substituted with C 1  -C 2  alkoxy, OH, 1-3 halogens, or C 1  -C 2  alkylthio; CH 2  (C 3  -C 4  cycloalkyl); C 3  -C 4  cycloalkyl optionally substituted with 1-3 methyl groups; C 2  -C 4  alkenyl; or C 2  -C 4  haloalkenyl; R 2  is H; chlorine; bromine; C 1  -C 2  alkyl; C 1  -C 2  alkoxy; C 1  -C 2  alkylthio; C 2  -C 3  alkoxyalkyl; C 1  -C 2  alkylthioalkyl; cyano; nitro; NH(C 1  -C 2  alkyl); or N(C 1  -C 2  alkyl) 2  ; R 4  is H; CH 3  ; or OCH 3  ; and agriculturally suitable salts thereof.

This application is a 371 of PCT/US94/10342 filed Sep. 12, 1994.

This invention relates to certain heteroaryl substituted anilides which are useful as herbicides and their agriculturally suitable compositions as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. Them are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

WO93/11097 discloses herbicidal anilide derivatives wherein an optionally substituted phenyl group occupies the ortho-position. In contrast, the compounds of the present invention bear a heteroaromatic group at that location and are therefore not disclosed therein.

SUMMARY OF THE INVENTION

The invention comprises compounds of Formula I: ##STR2## X is a single bond; O; S; or NR⁴ ; Y is O; S; or NCH₃ ;

Z is CH or N;

W is CH or N;

R¹ is C₁ -C₅ alkyl optionally substituted with C₁ -C₂ alkoxy, OH, 1-3 halogens, or C₁ -C₂ alkylthio; CH2(C₃ -C₄ cycloalkyl); C₃ -C₄ cycloalkyl optionally substituted with 1-3 methyl groups; C₂ -C₄ alkenyl; C₂ -C₄ haloalkenyl; or optionally substituted phenyl;

R² is H; chlorine; bromine; C₁ -C₂ alkyl; C₁ -C₂ alkoxy; C₁ -C₂ alkylthio; C₂ -C₃ alkoxyalkyl; C₂ -C₃ alkylthioalkyl; cyano; nitro; NH(C₁ -C₂ alkyl); or N(C₁ -C₂ alkyl)₂ ;

R³ is C₁ -C₄ haloalkyl; C₁ -C₄ haloalkoxy; C₁ -C₄ haloalkylthio; halogen; cyano; nitro; or methylthio;

R⁴ is H; CH₃ or OCH₃ ; and agriculturally suitable salts thereof.

Preferred compounds of Formula I for reasons of greatest herbicidal activity and/or ease of synthesis are:

1. Compounds of Formula I wherein:

R¹ is C₁ -C₄ alkyl optionally substituted with methoxy or 1-3 halogens; C₂ -C₄ alkenyl; or C₂ -C₄ haloalkenyl;

R² is chlorine; bromine; C₁ -C₂ alkyl; C₁ -C₂ alkoxy; cyano; nitro; NH(C₁ -C₂ alkyl); or N(C₁ -C₂ alkyl)₂.

2. Compounds of Preferred 1 wherein:

X is a single bond;

R³ is C₁ -C₂ haloalkyl; C₁ -C₂ haloalkoxy; C₁ -C₂ haloalkylthio; chlorine or bromine.

3. Compounds of Preferred 2 wherein:

Q is Q-1 or Q-2.

Specifically preferred for greatest herbicidal activity and/or ease of synthesis are: 2-methyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyridinyl]phenyl]-propanamide; and

2-methyl-N-[4-methyl-2-[2-(trifluoromethylthio)-4-pyrimidinyl]-phenyl]-propanamide.

Further embodiments of the invention include:

A composition for controlling growth of undesired vegetation comprising a herbicidally effective mount of a compound of Formula I as defined herein and at least one of a surfactant, solid or liquid diluent.

A method of controlling the growth of undesired vegetation comprising applying to the locus to be protected a herbicidally effective amount of the composition described above.

DETAILED DESCRIPTION OF THE INVENTION

Compounds of General Formula I can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 1-7 of this section as well as by following the specific procedures given in Examples 1-13. The definitions of Q, X, Y, Z and R¹ -R⁴ are as described in the Summary of the Invention.

Scheme 1 illustrates the preparation of compounds of Formula I whereby substituted phenyl compounds of Formula IIa wherein X² is triakyltin (e.g., Me₃ Sn), triakylsilyl (e.g., Me₃ Si), or a boronic acid derivative (e.g., B(OH)₂) are coupled with heterocycles of Formula Ilia wherein X¹ is chlorine, bromine, iodine or trifluoromethylsulfonyloxy (OTf). The coupling is carried out by methods known in the art: for example, see Tsuji, J., Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin (1980); Negishi, E., Acc. Chem. Res. (1982), 15, 340; Stille, J. K., Angew. Chem. (1986), 98, 504; Yamamoto, A. and Yamagi, A., Chem. Pharm. Bull. (1982), 30, 1731 and 2003; Dondoni et at., Synthesis (1987), 185; Dondoni et al., Synthesis (1987), 693; Hoshino et al., Bull. Chem. Soc. Jpn. (1988), 61, 3008; Sato, M. et al., Chem. Left. (1989), 1405; Miyaura et al., Synthetic Commun. (1981), 11,513; Siddiqui and Sniekus, Tetrahedron Lat. (1988), 29, 5463; Sharp at al., Tetrahedron Lett. (1987), 28, 5093; Hatanaka et at., Chem. Lett., (1989), 1711; Bailey, T. R., Tetrahedron Lett. (1986), 27, 4407, Echavarren, A. M. and Stille, J. K., J. Am. Chem. Soc. (1987), 109, 5478, and Ali et al., Tetrahedron Lat. (1992), 48, 8117. The coupling of IIa and IIIa is carried out by heating the mixture in the presence of a transition metal catalyst such as tetrakis(triphenylphosphine) palladium(O) or bis(triphenylphosphine)-palladium (11) dichloride in a solvent such as toluene, acetonitrile, glyme, or tetrahydrofuran optionally in the presence of an aqueous inorganic base such as sodium hydrogen carbonate or an organic base such as triethylamine. One skilled in the art will recognize that when IIIa contains more than one reactive substituent, then the stoichlometric ratios of reagents will need to be adjusted to minimize his-coupling. ##STR3##

Conversely, the anilides of Formula I can be prepared by reversing the reactivity of the two substrates. Substituted phenyl compounds of Formula lib wherein X² is chlorine, bromine, iodine or trifluoromethylsulfonyloxy (OTf) can be coupled with heteroaromatic compounds of Formula IIIb wherein X¹ is trialkyltin (e.g., Me₃ Sn), trialkylsilyl (e.g., Me₃ Si), or a boronic acid derivative (e.g., B(OH)₂). The procedure for conducting the coupling is the same as those described and referenced above.

By methods also reported in the above cited literature, compounds of Formula IIa and IIIb are prepared by treating the corresponding halide (i.e., wherein X¹ and X² is bromine or iodine) with a metalating agent such as n-butyllithium followed by quenching with a trialkyltin halide, trialkylsilyl halide, boron trichloride, or trialkyl borate.

Some compounds of Formula IIa can also be prepared from the corresponding ortho-unsubstituted compound (i.e., wherein X² is hydrogen) by treatment with a base such as n-butyllithium followed by quenching with a trialkyltin halide, trialkylsilyl halide, or trialkyl borate as reported in the same literature references. This preparation requires that --NHC(═O)XR¹ is an ortho-metalation directing group known in the an (e.g., trimethylacetylamido): see for example, Fuhrer, W., J. Org. Chem., (1979), 44, 1133.

Anilides and heteroaromatics of Formula II and III wherein X¹ and X² are chlorine, bromine, iodine, OTf, and hydrogen are either known or readily prepared by procedures and techniques well known in the art, for example: Houben-Weil, Methoden der Organische Chemie, IV edition, Eugen Muller, Ed., Georg Thieme Verlag; Turchi, I. J., The Chemistry of Heterocyclic Compounds, Vol. 45, pp. 36-43, J. Wiley & Sons, New York (1986); L. S. Wittenbrook, G. L. Smith, R. J. Timmons, J Org. Chem. (1973), 38, 465-471; and P. Reynaud, et al., Bull. Soc. Chim. Fr. (1962), 1735-1738.

Compounds of Formula I can also be prepared by one skilled in the art from anilines of Formula IV by treatment with an appropriate acyl chloride or acid anhydride (X═direct bond), chloroformate (X═O), chlorothiolformates (X═S), carbamoyl chloride (X═NCH₃), or isocyanate (X═NH) under conditions well known in the literature, for example: Sandler, R. S. and Karo, W., Organic Functional Group Preparations, 2nd Edition, Vol. I, p 274 and Vol. H, pp 152, 260, Academic Press (Scheme 2). ##STR4##

Alternatively, anilines of Formula IV can be convened into the corresponding isocyanate by treatment with phosgene or known phosgene equivalents (e.g., C1C(═O)OCCl₃), and then condensed with an appropriate alcohol or amine of Formula V to afford anilides of Formula I (Scheme 3). These techniques are well known in the literature. For example, see Sandlet, R. S. and Karo, W., Organic Functional Group Preparations, 2nd Edition, Vol. II, 152, 260, Academic Press; Lehman, G. and Teichman, H. in Preparative Organic Chemistry, 472, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons, New York, (1972); Eckert, H. and Forster, B., Angew. Chem., Int. Ed., (1987), 26, 894; Babad, H. and Zeiler, A. G., Chem. Rev., (1973), 73, 75. ##STR5##

Anilines of Formula IV are readily prepared by palladium catalyzed coupling of an ortho-substituted nitrophenyl compound of Formula VIa, wherein X² is as defined above, with a heteroaromatic compound of Formula III, wherein X¹ is as defined above, followed by catalytic or chemical reduction of the nitro group (Scheme 4). As described for Scheme 1, the reactivity of the substrates can be reversed, i.e. the coupling is carded out using an ortho-substituted nitrophenyl compound of Formula VIb and a heteroaromatic compound of Formula IIIb.

Reduction of nitro groups to amino groups is well documented in the chemical literature. See for example, Ohme, R. and Zubek, A. R. and Zubek, A. in Preparative Organic Chemistry, 557, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons, New York: (1972). ##STR6##

In some cases, it is desirable to perform the palladium coupling reaction on an N-protected form of the aniline, for example the 2,2-dimethylpropanamide. Upon completion of the coupling reaction, the N-protecting group can be removed, for example by treatment of the 2,2-dimethylpropanamide with acid, to liberate the amino group.

In other cases, it is advantageous to prepare compounds of Formula IV, not by the cross-coupling methods described above, but rather by elaboration of a substituted ortho-nitrobenzoic acid, or a derivative thereof (Formula VII), under any of a number of ring closure methodologies (Scheme 5). Subsequent reduction of the nitro compounds of Formula VIII provides compounds of Formula IV. One skilled in the art will recognize that these same ring closure methodologies can be used to elaborate a substituted ortho-aminobenzoic acid, or a derivative thereof, into compounds of Formula IV. ##STR7## wherein X³ can be any of a number of heterocycle building blocks, including, but not limited to those shown below:

X³ ═CO2H, COCl, CO₂ -alkyl, CONH₂, C(═S)NH₂, CHO, CN, C(═NOH)NH₂, COCH₂ NH₂, and COCH₂ -halogen.

Compounds of Formula VII are well known in the art or may be made by simple functional group interconversions on ortho-substituted nitrobenzenes.

Numerous methods for conversion of these X³ substituents into 5-membered heterocycles are well known in the literature and can be applied by those skilled in the art for the preparation compounds of Formula VIII wherein Q is Q-3, Q-4, Q-5 or Q-6. For example, see A. R. Katritzky and C. W. Rees, Comprehensive Heterocyclic Chemistry, Vol. 6, pp. 216-222; 293-306; 386-391; 492-508, Pergamon Press, London (1984); R. Elderfield, Heterocyclic Compounds, Vol. 5, pp. 302-319; 495-505, J. Wiley & Sons, New York (1957); ibid., Vol. 7., pp. 508-518; 558-569, J. Wiley & Sons, New York (1961); I. J. Turehi, M. J. S. Dewar, Chem. Rev. (1975), 75(4), 389-436; A. M. Van Leusen, B. E. Hoogenboom, H. Siderius, Tetrahedron Lett. (1972), 2369-2372; F. Yokokawa, Y. Hamada, T. Shioiri, Synlett (1992), 153-155. This strategy is illustrated in Example 13.

In some instances, it may be necessary, or more convenient, to introduce the desired substituents after the coupling reaction was performed. This can be accomplished by electrophilic substitution (Scheme 6), or nucleophilic substitution and functional group modifications (Scheme 7) using procedures well documented in the literature. These strategies are illustrated in Examples 3-13. ##STR8##

Variation of the substituent R³ on the heterocycle Q of compounds of Formula I may be achieved by one of two ways. First, one skilled in the art may simply select the appropriate heteroaromatic compound of Formula III a, b for the palladium coupling in Schemes 1 and 4 to give examples with a variety of values for R³. Alternatively, it may at times be convenient to vary R³ by performing various functional group transformations on the previously assembled aryl-substituted heterocycle of Formula I as shown in Scheme 7. Methods to perform these transformations are well known in the literature. Some examples include conversion of chloro to bromo (L. J. Street, et al., J. Med. Chem. (1992), 35, 295-304), bromo to trifluoromethyl (J. Wrobel, et al., J. Med. Chem. (1989), 32(II), 2493-2500), cyano (G. P. Ellis, T. M. Romney-Alexander, Chem. Rev. (1987), 87, 779-794), alkoxy and alkylthio, aldehyde to difluoromethyl (W. J. Middleton, J. Org. Chem. (1975), 40, 574-578), thiol to trifluoromethylthio (V. I. Popov, V. N. Boiko, L. M. Yagupolskii, J. Fluor. Chem. (1982), 21, 365-369) and amino to a variety of substituents via the diazonium salts. Electrophilic aromatic substitution or metallation chemistry are also useful methods for incorporating certain substitutents. ##STR9##

One skilled in the art will recognize that the above methods may require the use of protecting groups or subsequent functional group interconversions to avoid undesired side reactions with substituents which may be sensitive to the reaction conditions. One skilled in the an will also recognize that compounds of Formula I and the intermediates described above can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever.

EXAMPLE 1 Preparation of N-(2-borono-4-methylphenyl)-2,2-dimethylpropanamide

A solution of 72.4 g N-(4-methylphenyl)-2,2-dimethylpropanamide in 1000 mL dry THF was cooled to -70° C. under nitrogen and 480 mL 2.5M nBuLi in hexanes was added dropwise over 1 h while maintaining the temperature below 60° C. Stirring was continued at -70° C. for 1 h, then the reaction was allowed to warm to room temperature with stirring overnight.

The reaction mixture was then cooled to -10° C. and 200 mL trimethyl borate was added dropwise while maintaining the temperature below 0° C. Stirring was continued at 0° C. for 2.5 h, 50 mL water was added dropwise over 0.5 h, and then concd. HCl was added to acidify the reaction. The solvents were removed in vacuo, 200 mL water added to form a slurry which was shaken (or stirred) thoroughly with ether. The white precipitate was collected by filtration, washed well with 1:1 ether/hexane mixture, then suspended in acetone and stirred for 20 min. While stirring, 600 mL water was added slowly in portions (more water may be necessary if precipitation is not complete). The white solid was collected by filtration, washed with water, then dried in a vacuum oven to yield 56.8 g of the title compound as a white powder. ¹ H NMR (CDCl₃): δ 1.03 (s,9H), 2.40 (s,3H), 7.20 (d, 1H), 7.80 (s,1H), 7.96 (d,1H), 9.8 (s,1H,NH).

EXAMPLE 2 Preparation of 2,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide

A mixture of 16 g (0.1 mol) 4-chloro-2-(methylthio)pyrimidine, 0.150 g palladium bis(triphenylphosphine) dichloride, and 30 mL dimethoxyethane was stirred under nitrogen for 20 min, 25.8 g (0.11 mol) N-(2-borono-4-methyl phenyl)-2,2-dimethylpropanamide and a solution of 26 g sodium bicarbonate in 300 mL water was added, and the resulting mixture was heated to reflux for 5 h. After cooling to 50° C., 50 mL ethyl acetate was added and the reaction mixture was stirred until it reached room temperature. The reaction mixture was diluted with 300 mL ethyl acetate and washed successively with water and brine. The organic extracts were dried over magnesium sulfate, faltered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 25.2 g of the title compound as white crystals melting at 119°-20° C. ¹ H NMR (CDCl₃): δ 1.28 (s,9H), 2.38 (s,3H), 2.60 (s,3H) 7.30-8.6 (5H), 11.3(s,1H,NH).

EXAMPLE 3 Preparation of 4-methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine

24 g 2,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide was dissolved in 120 mL glacial acetic acid and the mixture warmed to reflux when 60 mL 15% hydrochloric acid solution was gradually added. After the addition was completed, the reaction mixture was heated at reflux for 4 h. After cooling, volatiles were removed in vacuo, the residue was taken up in 200 mL water and ice was added. The resulting mixture was neutralized to pH 10 with 5% sodium hydroxide solution and extracted with ether. Organic extracts were washed with brine, dried, evaporated to dryness and then dried in a vacuum oven to yield 6.2 g of the title compound as a tan solid melting at 120°-123° C. ¹ H NMR (CDCl₃): δ 2.30 (s,3H), 2.60 (s,3H), 5.8 (s,2H,NH₂), 6.60-8.6 (5H).

EXAMPLE 4 Preparation of 2-methyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide

A solution of 11.7 g (0.11 mol) isovaleryl chloride in 15 mL dry chloroform was added dropwise with stirring to a solution of 23.1 g (0.10 mol) 4-methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine and 12 g pyridine in 60 mL dry chloroform. Stirring was continued for 1 h at room temperature, after which the reaction mixture was diluted with 200 mL ether and washed successively with water, 0.5N hydrochloric acid solution, and brine. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 10:1 chlorobutane/ethyl acetate mixture as eluent to yield 28.3 g of the title compound as white crystals melting at 134°-135° C. ¹ H NMR (CDCl₃): δ 1.23 (d,6H), 2.30 (s,3H), 2.40 (s,3H) 2.47 (m,1H), 7.40-8.6 (5H), 10.7(s,1H,NH).

EXAMPLE 5 Preparation of 2-methyl-N-[4-methyl-2-[2-(methylsulfonyl)-4-pyrimidinyl]phenyl]propanamide

A total of 7.6 g 50% meta-chloroperbenzoic acid was added in small portions at room temperature during 6 h to a solution of 6 g (0.02 mol) 2-methyl-N-[4-methyl-2-[2-(methylthio)4-pyrimidinyl]phenyl]propanamide in 75 mL chloroform. Stirring was continued overnight. The reaction mixture was diluted with 100 mL methylene chloride and washed successively with water, 1N sodium thiosulfate solution, 1N sodium hydroxide solution, and brine. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 10:1 chlorobutane/ethyl acetate mixture as eluent to yield 6.2 g of the title compound bright yellow crystals melting at 146°-149° C. ¹ H NMR (CDCl₃): δ 1.21 (d,6H), 2.40 (s,3H), 2.80 (m,1H) 3.40 (s,H), 7.40-8.80 (5H), 11.4 (s,1H,NH).

EXAMPLE 6 Preparation of N-[2-(2-mercapto-4-pyrimidinyl)-4-methylphenyl]-2-methylpropanamide

3.3 g (0.01 mol) 2-methyl-N-[4-methyl-2-[2-(methylsulfonyl)-4-pyrimidinyl]phenyl]propanamide was dissolved in 35 mL absolute ethanol and 3 g potassium hydrogen sulfide was added to this solution with stirring. The reaction mixture was stirred overnight at room temperature. 50 mL water was added and the volume reduced under vacuum to 40 mL. An additional 40 mL water was added and the solution thus obtained was made acidic with concentrated hydrochloric acid. The yellow precipitate was collected by filtration, washed with a little water, then dissolved in 50 mL 1N sodium hydroxide and treated with charcoal. The charcoal was filtered off and the filtrate was made acidic with concentrated hydrochloric acid. The bright yellow precipitate was collected by filtration, washed with water, then dried in a vacuum oven to yield 2.18 g of N-[2-(2-mercapto-4-pyrimidyl)-4-methylphenyl]-2-methylpropanamide. ¹ H NMR (CDCl₃): δ 1.21 (d,6H), 2.40 (s,3H), 2.75 (m,1H), 7.40-8.60 (5H), 11.4(s,1H,NH), 11.9(s,1H,SH).

EXAMPLE 7 Preparation of 2-methyl-N-[4-methyl-2-[2-[(trifluoromethyl)thio]-4-pyrimidinyl]phenyl]propanamide

2 g trifluoromethyl iodide was condensed into a solution of 0.57 g (0.002 mol) N-[2-(2-mercapto-4-pyrimidinyl)-4-methylphenyl]-2-methylpropanamide and 2.5 g triethylamine in 20 mL anhydrous acetonitrile, and the reaction mixture was stirred under a dry ice condenser while exposed to a sun lamp for 4 h. The reaction mixture was diluted with 100 mL ether and washed successively with water, 1N sodium hydroxide solution, and brine. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.52 g of the title compound as yellow crystals melting at 114°-116° C. ¹ H NMR (CDCl₃): δ 1.21 (d,6H), 2.40 (s,3H), 2.55 (m,1H), 7.40-8.70 (5H), 10.7(s,1H,NH).

EXAMPLE 8 Preparation of N-[2-[2-[(difluoromethyl)thiol]4-pyrimidinyl]4-methylphenyl]-2-methylpropanamide

0.290 g (0.001 mol) N-[2-(2-mercapto-4-pyrimidinyl)4-methylphenyl]-2-methylpropanamide was dissolved in 10 mL 5% sodium hydroxide solution, 5 mL dioxane and 0.030 g tetrabutylammonium hydrogen sulfate were then added, and difluorodichloromethane was bubbled through at slow rate for 5 min with slight exothermic reaction. The reaction mixture was further stirred at room temperature for 2 h after which it was diluted with 50 mL ether, washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 20:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.20 g of the rifle compound as yellow crystals melting at 128°-130° C. ¹ H NMR (CDCl₃): δ 1.21 (d,6H), 2.40 (s,3H), 2.55 (m,1H), 7.40-8.00 (t,1H), 7.40-8.60 (5H), (11.0 (s,1H,NH).

EXAMPLE 9 Preparation of 2,2-dimethyl-N-[4-methyl-2-[2-(2,2,2-trifluoroethoxy)-4-pyrimidinyl]phenyl]propanamide

0.10 g sodium metal was covered under nitrogen with 15 mL anhydrous tetrahydrofuran and 1 g trifluoroethanol was added dropwise with stirring. Stirring was continued for 1.5 h at which time the sodium was completely reacted. A solution of 0.4 g 2,2-dimethyl-N-[4-methyl-2-[2-(methylsulfonyl)-4-pyrimidinyl]phenyl]propanamide was added via syringe and stirring continued overnight under nitrogen. The reaction mixture was quenched with water and extracted with ether. The organic extracts were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.38 g of the title compound as white crystals melting at 126°-128° C. ¹ H NMR (CDCl₃): δ 1.28 (s,9H), 2.40 (s,3H), 4.85 (q,2H), 7.30-8.6 (5H), 11.9(s,1H,NH).

EXAMPLE 10 Preparation of N-[2-(6-bromo-2-pyridinyl)-4-methylphenyl]-2,2-dimethylpropanamide.

A mixture of 24 g (0.1 mol) 2,6-dibromopyridine, 0.250 g palladium bis(triphenylphosphine) dichloride, and 40 mL dimethoxyethane was stirred under nitrogen for 20 min, after which 12 g (0.05 mol) N-(2-borono4-methylphenyl)-2,2-dimethylpropanamide and a solution of 26 g sodium bicarbonate in 300 mL water was added, and the mixture heated to reflux for 5 h. After cooling to 50° C., 50 mL ethyl acetate was added and stirred until it reached room temperature. The reaction mixture was diluted with 300 mL ethyl acetate and washed successively with water and brine. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica using 20:1 chlorobutane/ethyl acetate mixture as eluent to yield 13.1 g of the title compound as light tan crystals melting at 120°-126° C. ¹ H NMR (CDCl₃): δ 1.28 (s,9H), 2.40 (s,3H), 7.30-8.4 (6H), 10.9 (s,1H,NH).

Starting 2,6-dibromopyridine was isolated as a fast running peak. A small amount of bis-coupling product, N,N'[2,6-pyridinediylbis-(4-methyl-2,1-phenylene)]bis[2,2-dimethylpropanamide] melting at 181°-184° C. was also obtained as a slower running peak. ¹ H NMR (CDCl₃): δ 1.28 (s, 18H), 2.40 (s,6H), 7.30-8.4 (9H), 10.7 (s,2H,NH).

EXAMPLE 11 Preparation of N-[4-bromo-2-[2-(trifluoromethyl)-4-pyrimidinyl]phenyl]-2,2-dimethylpropanamide

3 g N-[2-[2-(trifluoromethyl)4-pyrimidinyl]phenyl]-2,2-dimethylpropanamide was dissolved in 30 mL glacial acetic acid, 5 g anhydrous sodium acetate was added, and a solution of 2.8 g bromine in 5 mL acetic acid was added dropwise with stirring over 1 h. The reaction mixture was stirred at room temperature overnight, after which it was diluted with water. The precipitate was collected by filtration, washed well with water, then with hexane, and was dried in a vacuum oven overnight to yield 3.3 g of the title compound melting at 153°-157° C. ¹ H NMR (CDCl₃): δ 1.28 (s,9H), 7.40-8.4 (6H), 10.6 (s,1H,NH).

EXAMPLE 12 Preparation of 2,2-dimethyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyrazinyl)]phenyl]propanamide

Step A: N-[2-(6-Chloro-2-pyrazinyl)-4-methylphenyl]-2,2-dimethylpropanamide

To a stirred mixture of the title compound from Example 1 (3.9 g, 0.017 mol), 2,6-dichloropyrazine (10.0 g, 0.067 mol) and tetrakis(triphenylphospine)-palladium(0) (0.05 g) in glyme (ethylene glycol dimethyl ether, 150 mL) was added aqueous 1M sodium carbonate (67 mL), 0.067 mol). The mixture was heated to reflux and for 8 h. After cooling to room temperature, the mixture was poured into brine (300 mL). The layers were separated and the aqueous phase extracted with three 150 mL-portions of ethyl acetate. The combined organic layers were dried (MgSO₄) and evaporated. The residue was chromatographed on silica gel eluting with 20% ethyl acetate/hexane to furnish 4.0 g (78% of theory) of the title compound as a white solid melting at 80°-83° C. ¹ H NMR (300 MHz, CDCl₃) δ 10.75 (br s, 1H), 8.91 (s, 1H), 8.51-8.56 (m, 1H), 8.39-8.41 (m,1H), 7.46 (s, 1H), 7.29-7.33 (m, 1H), 2.40 (s, 3H), 1.32 (s, 9H).

Step B: N-[2-(6-Bromo-2-pyrazinyl)-4-methylphenyl]-2,2-dimethyl-propanamide

The product from Step A (2.0 g, 6.6 mmol) was dissolved in a 30% solution of hydrobromic acid/acetic acid (18.0 mL). This mixture was stirred at room temperature for four days. The mixture was poured into aqueous 1M sodium carbonate (150 mL) and then extracted with ethyl acetate (5×50 mL). The combined extracts were dried (MgSO₄) and then evaporated. The solid residue was recrystallized from hexane to afford 1.0 g (45%) of the title compound melting at 74°-76° C. ¹ H NMR (400 MHz, CDCl₃) δ 10.64 (br s, 1H), 8.92 (s, 1H), 8.66 (s, 1H), 8.38 (m, 1H), 729-7.43 (s, 1H), 7.29-7.32 (m, 1H), 2.39 (s, 3H), 1.33 (s, 9H). Mass spec (EI) m/e 349 (1XBr).

Step C: 2,2-Dimethyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyrazinyl]phenyl]propanamide

The product obtained from Step B (0.8 g, 2.3 mmol) was dissolved in N-methylpyrrolidinone (16 mL). Cuprous iodide (1.7 g, 9.2 mmol) and sodium trifluoroacetate (2.5 g, 18.4 mmol) were then added and the resultant mixture heated at 180° C. for 6 h. After cooling to room temperature, diethyl ether (200 mL) and water (100 mL) were added. The two-phase mixture was filtered through a pad of Celite and the filter cake subsequently washed with three 50 mL-portions of ether. The layers of the filtrate were separated and the ether layer dried (MgSO₄). The ethereal solution was evaporated and the residue chromatographed on silica gel eluting with 15% ethyl acetate/hexane. In this manner, 0.14 g (18%) of the title compound was obtained as a yellow semisolid. ¹ H NMR (300 MHz,CDCl₃) δ 10.25 (br s,1H), 9.18 (s,1H), 8.93 (s,1H), 8.33-8.35 (m,1H), 7.41 (s, 1H), 7.33-7.35 (m,1H), 2.41 (s,3H), 1.25 (s,9H). ¹⁹ F NMR (282 MHz, CDCl₃) δ 67.2.

EXAMPLE 13 Preparation of N-[4-methyl-2-[4-(trifluoromethyl)-2-thiazolyl]-phenyl]cyclopropanecarboxamide

Step A: 5-Methyl-2-nitrobenzamide

5-methyl-2-nitrobenzoic acid (25.0 g, 0.14 mol) was dissolved in diethyl ether (280 mL). To this solution at room temperature was added oxalyl chloride (12.1 mL, 0.14 mol) followed by a catalytic amount of N, N-dimethylformamide (4-5 drops). The solution was stirred for 2 h at room temperature. The reaction mixture was concentrated to give a quantitative yield of the acid chloride. This material was not purified further and was stored as a one molar solution in dichloromethane.

69 mL of the stock solution above (13.8 g, 0.069 mol of acid chloride) was added dropwise to a stirred methanolic solution of ammonia (Aldrich, 2M, 69 mL, 0.138 mol) at 0° C. After the addition was complete, the mixture was allowed to warm to room temperature and then stirred overnight. The solvents were removed under vacuum and the residue taken up in ethyl acetate (500 mL). The organic solution was washed with water (2×250 mL) and dried (MgSO₄). Concentration of the extracts and recrystallization of the residual solid from acetonitrile afforded 9.43 g (76% yield) of the title compound as a yellow solid melting at 172°-175° C. ¹ H NMR (400 MHz, DMSO-d₆) δ 8.07 (br s, 1H), 7.91-7.93 (m, 1H), 7.65 (br s, 1H), 7.45-7.47 (m, 1H), 7.43 (s, 1H), 2.42 (s, 3H).

Step B: 5-Methyl-2-nitrobenzenecarbothioamide

7.0 g (0.040 mol) of the product from Step A was suspended in toluene (140 mL). Lawesson's reagent (9.4 g, 0.023 mol) was added and the resulting mixture heated at 100° for 3 h (the mixture became homogeneous at 85° C.). After cooling to room temperature, the toluene was removed on the rotary evaporator. The residue was flash chromatographed on silica gel eluting with 20% ethyl acetate/hexane to furnish 7.2 g (95% yield) of the title compound as a yellow semisolid. ¹ H NMR (400 MHz, CDCl₃) δ 7.92-7.94 (d,1H), 7.93 (br s, 1H, overlap with doublet), 7.25-7.32 (m,2H), 7.17 (br s, 1H), 2.45 (s,3H).

Step C: 4,5-Dihydro-2-(5-methyl-2-nitrophenyl)-4-(trifluoromethyl)-4-thiazolol

The product from Step B (5.5 g, 0.028 mol) was dissolved in ethyl alcohol (100 mL). 3-bromo-1,1,1-trifluoroacetone (5.3 g, 0.028 mol) was added and the resulting solution refluxed for 3 h. After cooling to room temperature, the reaction mixture was evaporated to dryness. The residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate (200 mL each). The organic layer was separated, dried (MgSO₄) and then concentrated to give an oil. Flash chromatography of this oil on silica gel eluting with 20% ethyl acetate/hexane afforded a solid which was further purified by recrystallization from chlorobutane/hexane. Yield: 4.4 g (51%) of the title compound as a white solid melting at 148°-151° C. ¹ H NMR (300 MHz, CDCl₃) δ 7.96-7.98 (m,1H), 7.42-7.44 (m,2H), 3.86-3.89 (m,1H), 3.34 (s,1H), 2.49 (s,3H).

Step D: 2-(5-Methyl-2-nitrophenyl)-4-(trifluoromethyl)thiazole

The tertiary alcohol (3.9 g, 0.013 mol) obtained in Step C was refluxed for 3 h in toluene (60 mL) in the presence of a catalytic amount of p-toluenesulfonic acid (0.2 g). Azeotropic removal of water was achieved by employing a Dean-Starke trap. After cooling to room temperature, the toluene was removed under vacuum. The residue was taken up in ethyl acetate (200 mL) and washed with 10% aqueous sodium carbonate and brine (100 mL each). The dried (MgSO₄) solution was concentrated to give 2.5 g (68% yield) of the title compound as white solid melting at 98°-104° C. ¹ H NMR (300 MHz, CDCl₃) δ 7.91-7.94 (m,2H), 7.53 (s,1H), 7.43-7.46 (m,1H), 2.51 (s,3H).

Step E: 4-Methyl-2-[4-(trifluoromethyl)-2-thiazolyl]benzenamine

The product from Step D (3.1 g, 0.011 mol) was suspended in a mixture of glacial acetic acid (15 mL) and water (5 mL). The mixture was heated on a steam bath to a temperature of 65° C. Iron powder (1.9 g, 0.035 mol) was then added in small portions (exothermic). Care was taken during the addition to ensure that the temperature did not exceed 75° C. Once the iron had been added, heating at 75° C. was continued for another 10 min. The reaction mixture was hot-filtered onto 30 g cracked ice. After the ice melted, the aqueous mixture was extracted with dichloromethane (3×20 mL). The combined extracts were washed with saturated sodium bicarbonate and brine (30 mL each). The dried (MgSO₄) solution was concentrated to furnish 1.4 g (53% yield) of the title compound as a white solid melting at 100°-103° C. ¹ H NMR (400 MHz, CDCl₃) δ 7.62 (s,1H), 7.39 (s,1H), 7.03-7.05 (m,1H), 6.69-6.71 (m,1H), 5.82 (br s,2H), 2.28 (s,3H).

Step F: N-[4-Methyl-2-[4-trifluoromethyl)-2-thiazolyl]phenyl]cyclopropanecarboxamide

To a stirred solution of the product obtained in Step E (0.46 g, 1.8 mmol) and triethylamine (250 μL, 1.8 mmol) in anhydrous tetrahydrofuran (THF, 15 mL) cooled to 0° C. was added dropwise a solution of cyclopropanecarbonyl chloride (160 μL, 1.8 mmol) in THF (5 mL). The mixture was stirred at 0° C. for 30 min and then at room temperature overnight. The reaction mixture was filtered and the solids were washed with ethyl acetate. The filtrate was evaporated to dryness and the residue purified by recrystallization from hexane to yield 0.41 g (71% yield) of the title compound as a white solid melting at 155°-156° C. ¹ H NMR (400 MHz, CDCl₃) δ 11.75 (s,1H), 8.61-8.63 (m,1H), 7.76 (s, 1H), 7.55 (s,1H), 7.26-7.27 (m,1H), 2.37 (s,3H), 1.56-1.62 (m,2H), 1.07-1.13 (m,2H).

Examples of compounds of the invention are shown in Tables 1-5.

                                      TABLE 1                                      __________________________________________________________________________      ##STR10##                                                                     R.sup.2 = CH.sub.3, R.sup.3 = CF.sub.3, W = CH, Z = CH,                        __________________________________________________________________________     R=                                                                             CH.sub.3                                                                            CH.sub.2 SCH.sub.3                                                                    CH.sub.2 CH.sub.2 Br                                                                    C(CH.sub.3)CH.sub.2                                                                      CH(CH.sub.3).sub.2                              CH.sub.2 F                                                                          (CH.sub.2).sub.4 CH.sub.3                                                             (CH.sub.2).sub.3 CH.sub.3                                                               CH(CH.sub.3).sub.2 Br                                                                    CHC(CH.sub.3).sub.2                             CH.sub.2 CH.sub.3                                                                   cyclopropyl                                                                           CHBrCH(CH.sub.3).sub.2                                                                  C(CH.sub.3).sub.2 SCH.sub.3                                                              CH(CH.sub.3)CH.sub.2 Cl                         CH.sub.2 Br                                                                         cyclobutyl                                                                            CHC(CH.sub.2 Cl).sub.2                                                                  CH.sub.2 C(CH.sub.3)CH.sub.2                                                             C(CH.sub.3)CHBr                                 CHCl.sub.2                                                                          OCH.sub.2 CH.sub.3                                                                    CH.sub.2 -cyclopropyl                                                                   CH.sub.2 CH(CH.sub.3).sub.2                                                              1-Me-cyclopropyl                                OCH.sub.3                                                                           C(CH.sub.3).sub.3                                                                     CH.sub.2 OCH.sub.3                                                                      CHBrCH.sub.3                                                                             OCH(CH.sub.3).sub.2                             CF.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                  C(CH.sub.3).sub.2 OCH.sub.3                                                             2-Me-cyclopropyl                                                                         CH(CH.sub.3)SCH.sub.3                           __________________________________________________________________________     R.sup.2 = CH.sub.2 CH.sub.3, R.sup.3 = CF.sub.3, W = CH, Z = CH,               __________________________________________________________________________     R=                                                                             CH.sub.2 CHCl.sub.2                                                                   CH(CH.sub.3).sub.2                                                                    cyclopropyl                                                                            OCH(CH.sub.3).sub.2                                                                     1-Me-cyclopropyl                                C(CH.sub.3).sub.3                                                                     CH.sub.2 CH.sub.2 CF.sub.3                                                            C(CH.sub.3).sub.2 CH.sub.2 Cl                                                          CH.sub.2 CH(CH.sub.3).sub.2                                                             2-Me-cyclopropyl                                __________________________________________________________________________     R.sup.2 = CH.sub.3, R.sup.3 = Br, W = CH, Z = CH, R=                           __________________________________________________________________________     CH(CH.sub.3).sub.2                                                                      cyclopropyl                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                                 CHC(CH.sub.3).sub.2                             C(CH.sub.3).sub.3                                                                       CHFCH.sub.3                                                                             CH(CH.sub.3)CH.sub.2 CH.sub.3                                                               CHC(CH.sub.2 Cl).sub.2                          CCl.sub.2 CH.sub.3                                                                      CHCl.sub.2                                                                              C(CH.sub.3).sub.2 OCH.sub.3                                                                 CH(CH.sub.3)SCH.sub.3                           C(CH.sub.3).sub.2 Br                                                                             2-Me-cyclopropyl                                                                            OCH(CH.sub.3).sub.2                             __________________________________________________________________________     R.sup.2 = CH.sub.3, R.sup.3 = Cl, W = CH, Z = CH, R=                           __________________________________________________________________________     CH(CH.sub.3).sub.2                                                                   CH(CH.sub.3)SCH.sub.3                                                                   cyclopropyl                                                                               OCH(CH.sub.3).sub.2                                                                   CH.sub.2 CH(CH.sub.3).sub.2                   CHCl.sub.2                                                                           1-Me-cyclopropyl                                                                        C(CH.sub.3).sub.2 OCH.sub.3                                                               C(CH.sub.3).sub.3                                                                     CH.sub.2 CHCl.sub.2                                 2-Me-cyclopropyl                                                                        CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             C(CH.sub.3).sub.2 Br                                                                  CHC(CH.sub.3).sub.2                           __________________________________________________________________________     R           R.sup.2 R           R.sup.2                                        __________________________________________________________________________     R.sup.3 = CF.sub.3, W = CH, Z = CH                                             CHClCH.sub.3                                                                               H       cyclobutyl  Br                                             CH(CH.sub.3).sub.2                                                                         H       CH.sub.2 CHF.sub.2                                                                         Br                                             C(CH.sub.3).sub.3                                                                          H       CH(CH.sub.3).sub.2                                                                         NO.sub.2                                       CF.sub.3    H       CH.sub.2 CH(CH.sub.3).sub.2                                                                NO.sub.2                                       CH(CH.sub.3).sub.2                                                                         Br      C(CH.sub.3).sub.3                                                                          NO.sub.2                                       C(CH.sub.3).sub.3                                                                          Br      CH.sub.2 OCH.sub.3                                                                         OCH.sub.3                                      cyclopropyl Br      C(CH.sub.3).sub.2 OCH.sub.3                                                                SCH.sub.3                                      1-Me-cyclopropyl                                                                           Br      Ph          CH.sub.3                                       OCH(CH.sub.3).sub.2                                                                        Br                                                                 R.sup.3 = Br, W = CH, Z = CH                                                   CH.sub.2 CHCl.sub.2                                                                        H       1-Me-cyclopropyl                                                                           CH.sub.2 CH.sub.3                              C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              H       CF.sub.3    CH.sub.2 CH.sub.3                              CH(CH.sub.3).sub.2                                                                         H       C(CH.sub.3).sub.3                                                                          Br                                             C(CH.sub.3).sub.3                                                                          H       CH.sub.2 SCH.sub.3                                                                         CH.sub.2 SCH.sub.3                             cyclopropyl SCH.sub.3                                                          R.sup.3 = Cl, W = CH, Z = CH                                                   CH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H       CHC(CH.sub.2 Cl).sub.2                                                                     H                                              CHFCH.sub.3 CH.sub.2 CH.sub.3                                                                      CHC(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                             CCl.sub.2 CH.sub.3                                                                         CH.sub.2 CH.sub.3                                                                      CH(CH.sub.3).sub.2                                                                         NO.sub.2                                       C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              H                                                                  __________________________________________________________________________     R        R.sup.2                                                                              R.sup.3                                                                             R        R.sup.2                                                                               R.sup.3                                    __________________________________________________________________________     W = CH, Z = CH                                                                 C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             SCH.sub.3                                                                           1-Me-cyclopropyl                                                                        OCH.sub.3                                                                             SCF.sub.3                                  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCH.sub.3                                                                           2-Me-cyclopropyl                                                                        OCH.sub.3                                                                             SCF.sup.3                                  CF.sub.3 CH.sub.3                                                                             SCH.sub.3                                                                           CH.sub.2 CH(CH.sub.3).sub.2                                                             NO.sub.2                                                                              SCHF.sub.2                                 cyclobutyl                                                                              CH.sub.3                                                                             SCH.sub.3                                                                           C(CH.sub.3).sub.3                                                                       OCH.sub.2 CH.sub.3                                                                    SCHF.sub.2                                 W = N, Z = CH                                                                  C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             Cl   CF.sub.3 NO.sub.2                                                                              Br                                         CH.sub.3 CH.sub.3                                                                             Cl   OCH(CH.sub.3).sub.2                                                                     H      Br                                         CH.sub.2 CH.sub.3                                                                       CH.sub.2 CH.sub.3                                                                    Cl   C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                              CF.sub.3                                   (CH.sub.2).sub.3 CH.sub.3                                                               H     Cl   cyclopropyl                                                                             CH.sub.3                                                                              CF.sub.3                                   (CH.sub.2).sub.4 CH.sub.3                                                               Br    Cl   CF.sub.3 OCH.sub.3                                                                             CF.sub.3                                   CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             Cl   OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              CF.sub.3                                   CH.sub.2 CH(CH.sub.3).sub.2                                                             Br    Cl   cyclobutyl                                                                              H      CF.sub.3                                   C(CH.sub.3).sub.2 OCH.sub.3                                                             CH.sub.3                                                                             Cl   1-Me-cyclopropyl                                                                        CH.sub.2 CH.sub.3                                                                     CF.sub.3                                   CH.sub.2 SCH.sub.3                                                                      CH.sub.3                                                                             Cl   cyclopropyl                                                                             CH.sub.3                                                                              SCF.sub.3                                  cyclopropyl                                                                             NO.sub.2                                                                             Cl   CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                              SCF.sub.3                                  CF.sub.3 SCH.sub.3                                                                            Cl   cyclobutyl                                                                              SCH.sub.3                                                                             SCF.sub.3                                  OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                             Cl   C(CH.sub.3).sub.3                                                                       Br     SCF.sub.3                                  C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             Br   cyclopropyl                                                                             Br     SCF.sub.3                                  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             Br   OCH(CH.sub.3).sub.2                                                                     H      SCF.sub.3                                  CH.sub.2 F                                                                              CH.sub.3                                                                             Br   cyclopropyl                                                                             CH.sub.3                                                                              SCHF.sub.2                                 CH(CH.sub.3)SCH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                    Br   CF.sub.3 SCH.sub.3                                                                             SCHF.sub.2                                 2-Me-cyclopropyl                                                                        H     Br   OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              SCHF.sub.2                                 cyclopropyl                                                                             NO.sub.2                                                                             Br   cyclobutyl                                                                              CH.sub.2 CH.sub.3                                                                     SCHF.sub.2                                 CHF.sub.2                                                                               SCH.sub.3                                                                            Br   1-Me-cyclopropyl                                                                        H      SCHF.sub.2                                 OCH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             Br   cyclopropyl                                                                             OCH.sub.3                                                                             NO.sub.2                                   __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR11##                                                                     R        R.sup.2                                                                             R.sup.3                                                                              R        R.sup.2                                                                              R.sup.3                                     __________________________________________________________________________     Z = CH                                                                         CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            CF.sub.3                                                                             CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCH.sub.3                                   CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                            CF.sub.3                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             H     SCH.sub.3                                   C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            CF.sub.3                                                                             C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             SCH.sub.3                                   C(CH.sub.3)OCH.sub.3                                                                    H    CF.sub.3                                                                             C(CH.sub.3)OCH.sub.3                                                                    H     SCH.sub.3                                   CHFCH.sub.3                                                                             CH.sub.3                                                                            CF.sub.3                                                                             CHFCH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                    SCH.sub.3                                   CF.sub.3 CH.sub.3                                                                            CF.sub.3                                                                             CF.sub.3 CH.sub.3                                                                             SCH.sub.3                                   CH.sub.2 CHCl.sub.2                                                                     H    SCH.sub.3                                                                            CCl.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             SCH.sub.3                                   C(CH.sub.3).sub.2 Br                                                                    CH.sub.3                                                                            SCH.sub.3                                                                            C(CH.sub.3).sub.2 CH.sub.2 Cl                                                           CH.sub.2 CH.sub.3                                                                    SCH.sub.3                                   cyclopropyl                                                                             CH.sub.3                                                                            SCH.sub.3                                                                            1-Me-cyclopropyl                                                                        CH.sub.3                                                                             SCH.sub.3                                   2-Me-cyclopropyl                                                                        CH.sub.3                                                                            SCH.sub.3                                                                            CHC(CH.sub.3).sub.2                                                                     CH.sub.3                                                                             SCH.sub.3                                   CHC(CH.sub.2 Cl).sub.2                                                                  CH.sub.3                                                                            SCH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCHF.sub.2                                  OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                            SCH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCF.sub.3                                   C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            SCHF.sub.2                                                                           CF.sub.3 CH.sub.3                                                                             SCF.sub.3                                   C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            SCF.sub.3                                                                            CHC(CH.sub.3).sub.2                                                                     SCH.sub.3                                                                            SCF.sub.3                                   C(CH.sub.3).sub.3                                                                       OCH.sub.3                                                                           SCF.sub.3                                                                            2-Me-cyclopropyl                                                                        CH.sub.2 OCH.sub.3                                                                   NO.sub.2                                    cyclopropyl                                                                             CH.sub.3                                                                            NO.sub.2                                                                             CH(CH.sub.3).sub.2                                                                      Br    Cl                                          C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            Cl    cyclopropyl                                                                             CH.sub.3                                                                             Cl                                          CF.sub.3 CH.sub.2 CH.sub.3                                                                   Cl    CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                             Cl                                          1-Me-cyclopropyl                                                                        Cl   Cl    CHC(CH.sub.3).sub.2                                                                     CH.sub.3                                                                             Cl                                          cyclopropyl                                                                             NO.sub.2                                                                            Cl    cyclopropyl                                                                             CH.sub.3                                                                             OCH.sub.2 CF.sub.3                          C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                   CH.sub.2 CH(CH.sub.3).sub.2                                                             OCH.sub.3                                                                            OCF.sub.3                                   CH(CH.sub.3).sub.3                                                                      CH.sub.3                                                                            OCF.sub.3                                                                            CHFCH.sub.3                                                                             CH.sub.3                                                                             OCF.sub.3                                   C(CH.sub.3)OCH.sub.3                                                                    CH.sub.3                                                                            OCF.sub.3                                                                            C(CH.sub.3).sub.2 Br                                                                    CH.sub.2 CH.sub.3                                                                    OCF.sub.3                                   CCl.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            OCF.sub.3                                                                            cyclopropyl                                                                             CH.sub.3                                                                             OCF.sub.3                                   C(CH.sub.3).sub.3                                                                       Cl   OCF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             NO.sub.2                                    CHC(CH.sub.3).sub.2                                                                     Br   OCF.sub.3                                                        cyclobutyl                                                                              CH.sub.3                                                                            NO.sub.2                                                                             CF.sub.3 CH.sub.2 CH.sub.3                                                                    NO.sub.2                                    OCH(CH.sub.3).sub.2                                                                     Br   NO.sub.2                                                                             cyclopropyl                                                                             Cl    NO.sub.2                                    C.sub.6 H.sub.5                                                                         CH.sub.3                                                                            CF.sub.3                                                         Z = N                                                                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            CF.sub.3                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                             CF.sub.3                                    C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            CF.sub.3                                                                             CHFCH.sub.3                                                                             CH.sub.3                                                                             CF.sub.3                                    CF.sub.3 CH.sub.3                                                                            CF.sub.3                                                                             OCH(CH.sub.3).sub.2                                                                     Br    CF.sub.3                                    cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   CF.sub.3                                                                             2-Me-cyclopropyl                                                                        NO.sub.2                                                                             CF.sub.3                                    CH(CH.sub.3).sub.2                                                                      Cl   CF.sub.3                                                                             OCH(CH.sub.3).sub.2                                                                     Cl    CF.sub.3                                    C(CH.sub.3).sub.3                                                                       CN   CF.sub.3                                                                             CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCH.sub.3                                   CF.sub.3 CH.sub.3                                                                            SCH.sub.3                                                                            CH.sub.2 CHCl.sub.2                                                                     Br    SCH.sub.3                                   CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            SCHF.sub.2                                                                           C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             SCHF.sub.2                                  CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            SCF.sub.3                                                                            C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             SCF.sub.3                                   CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                            SCF.sub.3                                                                            OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                             SCF.sub.3                                   CF.sub.3 CH.sub.3                                                                            SCF.sub.3                                                                            cyclopropyl                                                                             Br    SCF.sub.3                                   1-Me-cyclopropyl                                                                        NO.sub.2                                                                            SCF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      Cl    SCF.sub.3                                   C(CH.sub.3).sub.3                                                                       CH.sub.2 CH.sub.3                                                                   SCF.sub.3                                                                            C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             Cl                                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            Cl    CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                             Cl                                          C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            Cl    CHFCH.sub.3                                                                             CH.sub.3                                                                             Cl                                          CF.sub.3 CH.sub.3                                                                            Cl    OCH(CH.sub.3).sub.2                                                                     Br    Cl                                          cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   Cl    2-Me-cyclopropyl                                                                        NO.sub.2                                                                             Cl                                          CH(CH.sub.3).sub.2                                                                      Cl   Cl    OCH(CH.sub.3).sub.2                                                                     Cl    Cl                                          C(CH.sub.3).sub.3                                                                       CN   Cl    CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             Br                                          CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                            Br    C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             Br                                          CHF.sub.2                                                                               CH.sub.3                                                                            Br    CF.sub.3 CH.sub.3                                                                             Br                                          OCH.sub.3                                                                               Br   Br    cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                    Br                                          1-Me-cyclopropyl                                                                        NO.sub.2                                                                            Br    CH(CH.sub.3).sub.2                                                                      Cl    Br                                          OCH(CH.sub.3).sub.2                                                                     Cl   Br    OCH.sub.2 CH.sub.3                                                                      CN    Br                                          CF.sub.3 CH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                   OCH(CH.sub.3).sub.2                                                                     Br    OCH.sub.2 CF.sub.3                          cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   OCH.sub.2 CF.sub.3                                                                   CH(CH.sub.3).sub.2                                                                      Cl    OCH.sub.2 CF.sub.3                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            NO.sub.2                                                                             cyclobutyl                                                                              CH.sub.3                                                                             NO.sub.2                                    C.sub.2 F.sub.5                                                                         CH.sub.3                                                                            NO.sub.2                                                                             OCH(CH.sub.3).sub.2                                                                     Br    NO.sub.2                                    cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   NO.sub.2                                                                             2-Me-cyclopropyl                                                                        CH.sub.3                                                                             OCF.sub.3                                   CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            OCF.sub.3                                                                            OCH(CH.sub.3).sub.2                                                                     Cl    OCF.sub.3                                   C(CH.sub.3).sub.3                                                                       Br   OCF.sub.3                                                        __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR12##                                                                     R        R.sup.2                                                                            R.sup.3                                                                            R        R.sup.2                                                                              R.sup.3                                        __________________________________________________________________________     Z.sup.1 = O                                                                    C(CH.sub.3)OCH.sub.3                                                                    H   CF.sub.3                                                                           CHFCH.sub.3                                                                             H     CF.sub.3                                       CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                           CF.sub.3                                                                           C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                             CF.sub.3                                       cyclopropyl                                                                             CH.sub.3                                                                           CF.sub.3                                                                           OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                             CF.sub.3                                       CH.sub.2 CH(CH.sub.3).sub.2                                                             Br  CF.sub.3                                                                           CF.sub.3 Br    CF.sub.3                                       C.sub.6 H.sub.5                                                                         Cl  CF.sub.3                                                                           CH.sub.2 CHCl.sub.2                                                                     NO.sub.2                                                                             CF.sub.3                                       1-Me-cyclopropyl                                                                        CN  CF.sub.3                                                                           C(CH.sub.3).sub.2 Br                                                                    CH.sub.3                                                                             SCH.sub.3                                      2-Me-cyclopropyl                                                                        H   SCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCHF.sub.2                                     C(CH.sub.3).sub.3                                                                       H   SCF.sub.3                                                                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCF.sub.3                                      CF.sub.3 Cl  SCF.sub.3                                                                          C(CH.sub.3).sub.3                                                                       OCH.sub.3                                                                            SCF.sub.3                                      CHC(CH.sub.3).sub.2                                                                     SCH.sub.3                                                                          SCF.sub.3                                                                          cyclopropyl                                                                             CH.sub.3                                                                             NO.sub.2                                       cyclobutyl                                                                              H   NO.sub.2                                                                           CH.sub.2 CF.sub.3                                                                       CH.sub.3                                                                             NO.sub.2                                       CH(CH.sub.3).sub.2                                                                      Br  Cl  CF.sub.3 CH.sub.2 CH.sub.3                                                                    Cl                                             cyclopropyl                                                                             CH.sub.3                                                                           Cl  OCH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             Br                                             CH.sub.2 CF.sub.3                                                                       Br  Br  cyclopropyl                                                                             CH.sub.3                                                                             OCH.sub.2 CF.sub.3                             CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                           OCF.sub.3                                                                          cyclopropyl                                                                             CH.sub.3                                                                             OCF.sub.3                                      CH.sub.2 CH(CH.sub.3).sub.2                                                             OCH.sub.3                                                                          OCF.sub.3                                                                          OCH.sub.3                                                                               CH.sub.2 CH.sub.3                                                                    CF.sub.2 Cl                                    CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                           CF.sub.2 Cl                                                                        cyclobutyl                                                                              Br    CF.sub.2 Cl                                    Z.sup.1 = S                                                                    C(CH.sub.3).sub.3                                                                       H   CF.sub.3                                                                           CH(CH.sub.3).sub.2                                                                      SCH.sub.3                                                                            CF.sub.3                                       cyclopropyl                                                                             CH.sub.3                                                                           CF.sub.3                                                                           CF.sub.3 Br    CF.sub.3                                       C.sub.6 H.sub.5                                                                         Cl  CF.sub.3                                                                           CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCHF.sub.2                                     cyclobutyl                                                                              H   SCF.sub.3                                                                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             SCF.sub.3                                      C(CH.sub.3).sub.3                                                                       SCH.sub.3                                                                          SCF.sub.3                                                                          2-Me-cyclopropyl                                                                        CH.sub.2 OCH.sub.3                                                                   NO.sub.2                                       CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                           NO.sub.2                                                                           cyclopropyl                                                                             CH.sub.3                                                                             Br                                             OCH(CH.sub.3).sub.2                                                                     Br  Br  CH.sub.2 CH(CH.sub.3).sub.2                                                             CN    Cl                                             1-Me-cyclopropyl                                                                        NO.sub.2                                                                           Cl  C(CH.sub.3).sub.3                                                                       Cl    OCF.sub.3                                      CHC(CH.sub.3).sub.2                                                                     Br  OCF.sub.3                                                                          CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             OCHF.sub.2                                     cyclopropyl                                                                             CH.sub.3                                                                           CF.sub.2 Cl                                                                        C.sub.6 H.sub.5                                                                         H     CF.sub.2 Cl                                    __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR13##                                                                     R        R.sup.2                                                                             R.sup.3                                                                              R        R.sup.2                                                                             R.sup.3                                      __________________________________________________________________________     Z.sup.1 = O                                                                    C(CH.sub.3).sub.3                                                                       H    CF.sub.3                                                                             OCH.sub.3                                                                               H    CF.sub.3                                     CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            CF.sub.3                                                                             OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                            CF.sub.3                                     CH.sub.2 CH(CH.sub.3).sub.2                                                             Cl   CF.sub.3                                                                             CF.sub.3 Cl   CF.sub.3                                     1-Me-cyclopropyl                                                                        Cl   CF.sub.3                                                                             C.sub.6 H.sub.5                                                                         Br   CF.sub.3                                     CH.sub.2 CHCl.sub.2                                                                     NO.sub.2                                                                            CF.sub.3                                                                             1-Me-cyclopropyl                                                                        C    CF.sub.3                                     C(CH.sub.3).sub.2 Br                                                                    CH.sub.3                                                                            SCH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            SCHF.sub.2                                   C(CH.sub.3).sub.3                                                                       H    SCF.sub.3                                                                            CHC(CH.sub.3).sub.2                                                                     SCH.sub.3                                                                           SCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      Br   SCF.sub.3                                                                            CF.sub.3 Cl   SCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      Br   Cl    CF.sub.3 CH.sub.2 CH.sub.3                                                                   Cl                                           cyclopropyl                                                                             CH.sub.3                                                                            Cl    OCH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            Br                                           CH.sub.2 CF.sub.3                                                                       Br   Br    OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                            OCH.sub.2 CF.sub.3                           OCH.sub.3                                                                               CH.sub.2 CH.sub.3                                                                   OCF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            OCF.sub.3                                    cyclobutyl                                                                              Br   OCF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            CF.sub.2 Cl                                  cyclopropyl                                                                             CH.sub.3                                                                            CF.sub.2 Cl                                                                          CH.sub.2 CH(CH.sub.3).sub.2                                                             OCH.sub.3                                                                           CF.sub.2 Cl                                  cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   NO.sub.2                                                                             CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            NO.sub.2                                     Z.sup.1 = S                                                                    C(CH.sub.3).sub.3                                                                       H    CF.sub.3                                                                             CH.sub.3 CH.sub.3                                                                            CF.sub.3                                     cyclopropyl                                                                             CH.sub.3                                                                            CF.sub.3                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                            CF.sub.3                                     CF.sub.3 Br   CF.sub.3                                                                             C.sub.6 H.sub.5                                                                         Cl   CF.sub.3                                     CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            SCHF.sub.2                                                                           cyclobutyl                                                                              H    SCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            SCF.sub.3                                                                            C(CH.sub.3).sub.3                                                                       SCH.sub.3                                                                           SCF.sub.3                                    cyclopropyl                                                                             CH.sub.3                                                                            NO.sub.2                                                                             cyclobutyl                                                                              H    NO.sub.2                                     CH.sub.2 CF.sub.3                                                                       CH.sub.3                                                                            NO.sub.2                                                                             C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            Br                                           CH(CH.sub.3).sub.2                                                                      H    Br    OCH.sub.2 CH.sub.3                                                                      NO.sub.2                                                                            Br                                           CH.sub.2 CH(CH.sub.3).sub.2                                                             CN   Cl    1-Me-cyclopropyl                                                                        CH.sub.3                                                                            Cl                                           cyclopropyl                                                                             CH.sub.3                                                                            OCF.sub.3                                                                            C.sub.6 H.sub.5                                                                         CN   OCF.sub.3                                    OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                            OCHF.sub.2                                                                           C(CH.sub.3).sub.3                                                                       NO.sub.2                                                                            CF.sub.2 Cl                                  CH(CH.sub.3).sub.2                                                                      Br   CF.sub.2 Cl                                                                          C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            CN                                           W = S, Z = CH                                                                  C(CH.sub.3).sub.3                                                                       H    CF.sub.3                                                                             OCH.sub.3                                                                               H    CF.sub.3                                     C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            SCH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            CF.sub.3                                     OCH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                            CF.sub.3                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             Cl   CF.sub.3                                     CF.sub.3 Cl   CF.sub.3                                                                             1-Me-cyclopropyl                                                                        Cl   CF.sub.3                                     C.sub.6 H.sub.5                                                                         Br   CF.sub.3                                                                             CH.sub.2 CHCl.sub.2                                                                     NO.sub.2                                                                            CF.sub.3                                     1-Me-cyclopropyl                                                                        CN   CF.sub.3                                                                             CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            SCHF.sub.2                                   C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            SCH.sub.3                                                                            CHC(CH.sub.3).sub.2                                                                     SCH.sub.3                                                                           SCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      Br   SCF.sub.3                                                                            CF.sub.3 Cl   SCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      Br   Cl    CF.sub.3 CH.sub.2 CH.sub.3                                                                   Cl                                           cyclopropyl                                                                             CH.sub.3                                                                            Cl    OCH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            Br                                           CH.sub.2 CF.sub.3                                                                       Br   Br    OCH(CH.sub.3).sub.2                                                                     CN   OCH.sub.2 CF.sub.3                           C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                               CH.sub.2 CH.sub.3                                                                   OCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            OCF.sub.3                                                                            cyclobutyl                                                                              Br   OCF.sub.3                                    CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            CF.sub.2 Cl                                                                          cyclopropyl                                                                             CH.sub.3                                                                            CF.sub.2 Cl                                  CH.sub.2 CH(CH.sub.3).sub.2                                                             OCH.sub.3                                                                           CF.sub.2 Cl                                                                          cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   NO.sub.2                                     CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            NO.sub.2                                                         W = S, Z = N                                                                   C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                            SCH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      Br   CF.sub.3                                     cyclopropyl                                                                             SCH.sub.3                                                                           CHF.sub.2                                                                            CF.sub.3 H    Br                                           CH.sub.2 CHCl.sub.2                                                                     CH.sub.2 CH.sub.3                                                                   OCF.sub.3                                                                            C.sub.6 H.sub.5                                                                         Cl   SCF.sub.3                                    W = O, Z = N                                                                   1-Me-cyclopropyl                                                                        Cl   CF.sub.2 Cl                                                                          CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                            CF.sub.3                                     cyclopropyl                                                                             CH.sub.2 CH.sub.3                                                                   NO.sub.2                                                                             CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                            Br                                           OCH.sub.3                                                                               CH.sub.2 CH.sub.3                                                                   OCF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      NO.sub.2                                                                            SCF.sub.3                                    cyclobutyl                                                                              Br   OCF.sub.3                                                                            CHBrCH.sub.3                                                                            H    Cl                                           __________________________________________________________________________

Formulation/Utility

Compounds of this invention will generally be used in a formulation or a composition comprising an agriculturally suitable carrier comprising at least one of a surfactant, a liquid or solid diluent or an organic solvent. Useful formulations include dusts, films, granules, pellets, solutions, suspensions, microencapsulations, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations or compositions will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

    ______________________________________                                                      Weight Percent                                                                 Active                                                                         Ingredient                                                                             Diluent   Surfactant                                      ______________________________________                                         Wettable Powders                                                                              5-90       0-74     1-10                                        Oil Suspensions,                                                                              5-50      40-95     0-15                                        Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Dusts          1-25      70-99     0-5                                         Granules and Pellets                                                                          0.01-99      5-99.99                                                                               0-15                                        High Strength Composi-                                                                        90-99      0-10     0-2                                         tions                                                                          ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, and the like.

Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.

For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 14; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et at., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A.

                  TABLE A                                                          ______________________________________                                         Example A                                                                      High Strength Concentrate                                                      Compound 1                 98.5%                                               silica aerogel              0.5%                                               synthetic amorphous fine silica                                                                            1.0%.                                              Example B                                                                      Wettable Powder                                                                Compound 1                 65.0%                                               dodecylphenol polyethylene glycol ether                                                                    2.0%                                               sodium ligninsulfonate      4.0%                                               sodium silicoaluminate      6.0%                                               montmorillonite (calcined) 23.0%.                                              Example C                                                                      Granule                                                                        Compound 1                 10.0%                                               attapulgite granules (low volatile                                                                        90.0%.                                              matter, 0.71/0.30 mm; U.S.S. No.                                               25-50 sieves)                                                                  Example D                                                                      Extruded Pellet                                                                Compound 1                 25.0%                                               anhydrous sodium sulfate   10.0%                                               crude calcium ligninsulfonate                                                                              5.0%                                               sodium alkylnaphthalenesulfonate                                                                           1.0%                                               calcium/magnesium bentonite                                                                               59.0%.                                              ______________________________________                                    

Tests results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to barley, cotton, wheat, rape, sugarbeets, corn, soybeans and rice. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control. Examples of other herbicides with which compounds of this invention can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benerin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenylacetamide, 2-chloroallyl diethyldithiocarbamate, chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clomazone, cloproxydim, clopyralid, calcium salt of methylarsonic acid, cyanazine, cycloate, cycluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichiobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, disodium salt of methylarsonic acid, dymron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flareprop, fluazifop, fluazifop-P, fluchloralin, flumesulam, flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluffdone, fluroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, haloxyfop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S'-dimethyl-2-(difluoromethyl)4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, salt of monuron and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(α, α-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, tri-allate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifiuralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, vernolate, and xylachlor.

In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for management of resistant weeds.

A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound(s) of this invention is applied at rates from about 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.

The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-E for compound descriptions.

                                      INDEX TABLE A                                __________________________________________________________________________      ##STR14##                                                                     Wherein R is XR.sup.1                                                          Cmpd.                                                                          No. R          R.sup.2                                                                              R.sup.3                                                                            W   Z   m.p. (°C.).sup.a                       __________________________________________________________________________     1   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  114-115                                       2   CH.sub.2 CH(CH.sub.3).sub.2                                                               CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  74-78                                         3   C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  136-145                                       4   CF.sub.3   CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  107-109                                       5   cyclopropyl                                                                               CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  104-106                                       6   1-Me-cyclopropyl                                                                          CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  149-151                                       7   2-Me-cyclopropyl                                                                          CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  113-115                                       8   cyclobutyl CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  84-86                                         9   CHC(CH.sub.3).sub.2                                                                       CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  101-106                                       10  CH.sub.2 C(CH.sub.3)CH.sub.2                                                              CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  78-81                                         11  OCH.sub.3  CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  111-113                                       12  OC.sub.2 H.sub.5                                                                          CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  100-104                                       13  OCH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  96-98                                         14  CH(CH.sub.3).sub.2                                                                        CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  106-108                                       15  CH.sub.2 CH(CH.sub.3).sub.2                                                               CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  90-91                                         16  C(CH.sub.3).sub.3                                                                         CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  130-133                                       17  cyclopropyl                                                                               CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  113-115                                       18  1-Me-cyclopropyl                                                                          CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  90-99                                         19  2-Me-cyclopropyl                                                                          CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  88-93                                         20  OCH(CH.sub.3).sub.2                                                                       CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                           CH  CH  79-81                                         21  CH(CH.sub.3).sub.2                                                                        H     CF.sub.3                                                                           CH  CH  80-81                                         22  C(CH.sub.3).sub.3                                                                         H     CF.sub.3                                                                           CH  CH  90-93                                         23  CH(CH.sub.3).sub.2                                                                        Br    CF.sub.3                                                                           CH  CH  108-117                                       24  C(CH.sub.3).sub.3                                                                         Br    CF.sub.3                                                                           CH  CH  153-157                                       25  cyclopropyl                                                                               Br    CF.sub.3                                                                           CH  CH  149-150                                       26  1-Me-cyclopropyl                                                                          Br    CF.sub.3                                                                           CH  CH  123-126                                       27  OCH(CH.sub.3).sub.2                                                                       Br    CF.sub.3                                                                           CH  CH  108-110                                       28  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             Br  CH  CH  57-60                                         29  CH.sub.2 CH(CH.sub.3).sub.2                                                               CH.sub.3                                                                             Br  CH  CH  oil                                           30  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             Br  CH  CH  120-126                                       31  2-Me-cyclopropyl                                                                          CH.sub.3                                                                             Br  CH  CH  77-80                                         32  CHC(CH.sub.3).sub.2                                                                       CH.sub.3                                                                             Br  CH  CH  163-167                                       33  OCH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                             Br  CH  CH  73-75                                         34  CH(CH.sub.3).sub.2                                                                        H     Br  CH  CH  76-80                                         35  C(CH.sub.3).sub.3                                                                         H     Br  CH  CH  oil                                           36  C(CH.sub.3).sub.3                                                                         Br    Br  CH  CH  138-141                                       37  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             Cl  CH  CH  oil                                           38  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             Cl  CH  CH  109-112                                       39  cyclopropyl                                                                               CH.sub.3                                                                             Cl  CH  CH  95-98                                         40  1-Me-cyclopropyl                                                                          CH.sub.3                                                                             Cl  CH  CH  104-107                                       41  2-Me-cyclopropyl                                                                          CH.sub.3                                                                             Cl  CH  CH  80-83                                         42  CHC(CH.sub.3).sub.2                                                                       CH.sub.3                                                                             Cl  CH  CH  174-178                                       43  CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             CH.sub.3                                                                             Cl  CH  CH  63-67                                         44  OCH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                             Cl  CH  CH  88-91                                         45  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             SCH.sub.3                                                                          CH  CH  81-86                                         46  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             SCH.sub.3                                                                          CH  CH  60-68                                         47  CF.sub.3   CH.sub.3                                                                             SCH.sub.3                                                                          CH  CH  108-110                                       48  Ph         CH.sub.3                                                                             CF.sub.3                                                                           CH  CH  156-157                                       49  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             Cl  N   CH  80-83                                         50  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             Br  N   CH  74-76                                         51  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             CF.sub.3                                                                           N   CH  wax                                           __________________________________________________________________________      .sup.a1 H NMR data for oils and waxes are given Index Table E.           

                  INDEX TABLE B                                                    ______________________________________                                          ##STR15##                                                                     Wherein R is XR.sup.1                                                          Cmpd                                                                           No.    R          R.sup.2 R.sup.3 Z    m.p. (°C.)                       ______________________________________                                         52     CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                               CF.sub.3                                                                               CH   112-114                                 53     C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                               CF.sub.3                                                                               CH   118-120                                 54     CF.sub.3   CH.sub.3                                                                               CF.sub.3                                                                               CH   135-138                                 55     CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                               SCH.sub.3                                                                              CH   134-135                                 56     C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                               SCH.sub.3                                                                              CH   119-120                                 57     CF.sub.3   CH.sub.3                                                                               SCH.sub.3                                                                              CH   181-183                                 58     cyclopropyl                                                                               CH.sub.3                                                                               SCH.sub.3                                                                              CH   120-123                                 59     OCH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                               SCH.sub.3                                                                              CH   78-82                                   60     CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                               SCHF.sub.2                                                                             CH   128-130                                 61     C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                               SCHF.sub.2                                                                             CH   119-125                                 62     CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                               SCF.sub.3                                                                              CH   114-116                                 63     C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                               SCF.sub.3                                                                              CH   124-128                                 64     C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                               Cl      CH   111-116                                 65     C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                     CH   126-128                                 66     Ph         CH.sub.3                                                                               CF.sub.3                                                                               CH   168-170                                 ______________________________________                                    

                  INDEX TABLE C                                                    ______________________________________                                          ##STR16##                                                                     Wherein R is XR.sup.1                                                          Cmpd                                                                           No.    R        R.sup.2                                                                               R.sup.3 W    Y    m.p. (°C.)                     ______________________________________                                         67     C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                              SCH.sub.3                                                                              N    S    115-117                               68     C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                     CH   S    104-107                               69     C(CH.sub.3).sub.3                                                                       CH.sub.3                                                                              SCH.sub.3                                                                              CH   S    95-98                                 ______________________________________                                    

                  Index TABLE D                                                    ______________________________________                                          ##STR17##                                                                     Cmpd                                                                           No     R            R.sup.2 R.sup.3                                                                             Y    m.p. (°C.)                        ______________________________________                                         70     C(CH.sub.3).sub.3                                                                           CH.sub.3                                                                               Br   S    75-78                                    71     C(CH.sub.3).sub.3                                                                           CH.sub.3                                                                               CN   S    204-206                                  72     CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3                                                                               CF.sub.3                                                                            S     96-100                                  73     cyclopropyl  CH.sub.3                                                                               CF.sub.3                                                                            S    155-156                                  74     CH.sub.3     CH.sub.3                                                                               CF.sub.3                                                                            S    130-133                                  ______________________________________                                    

    ______________________________________                                         Index TABLE E                                                                  Cmpd.                                                                          No.   .sup.1 H NMR Data.sup.a                                                  ______________________________________                                         29    1.00(d, 6H), 2.25(m, 3H), 2.40(s, 3H), 7.10-8.4(m 6H),                         11.5(s, 1H, NH).                                                         35    1.38(s, 9H), 7.10-8.4(m, 7H), 11.1(s, 1H, NH).                           37    1.3(d, 6H), 2.40(s, 3H), 2.60(m, 1H), 7.10-8.4(m, 6H),                         11.5(s, 1H, NH).                                                         51    1.25(s, 9H), 2.40(s, 3H), 7.33-9.18(m, 5H), 10.3(s, 1H,                  ______________________________________                                               NH).                                                                      .sup.a 1 H NMR data are in ppm downfield from tetramethylsilane. Coupling      are designated by ssinglet, ddoublet, mmultiplet. Samples dissolved in         CDCl.sub.3 unless otherwise indicated.                                   

TEST A

Seeds of barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), sorghum (Sorghum bicolor), velvetleaf (Abutilon theophrasti), and wild oat (Avena fatua) were planted into a sandy loam soil and treated preemergence or by soil drench with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated postemergence or sprayed to runoff, with test chemicals formulated in the same manner. Plants ranged in height from two to eighteen eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (--) response means no test results.

                  TABLE A                                                          ______________________________________                                         PREEMERGENCE                                                                                       COM-      COM-                                                                 POUND     POUND                                                    COMPOUND    51        74                                                         49    67    69  72  73  Rate    Rate                                         Rate 2000 g/ha                                                                             1000 g/ha 800 g/ha                                         ______________________________________                                         Barnyardgrass                                                                            3     0     1   1   1   4       0                                    Cocklebur 0     0     0   0   0   0       0                                    Crabgrass 8     0     2   2   2   7       0                                    Downy brome                                                                              0     0     0   0   0   0       0                                    Giant Foxtail                                                                            9     0     1   1   3   9       0                                    Morningglory                                                                             1     0     0   0   1   1       0                                    Sorghum   0     0     0   0   0   1       0                                    Velvetleaf                                                                               0     0     0   2   1   0       0                                    Wild Oat  0     0     0   0   0   0       0                                    ______________________________________                                         POSTEMERGENCE                                                                                      COM-      COM-                                                                 POUND     POUND                                                    COMPOUND    51        74                                                         49    67    69  72  73  Rate    Rate                                         Rate 1000 g/ha                                                                             500 g/ha  400 g/ha                                         ______________________________________                                         Barnyardgrass                                                                            3     0     3   1   2   2       1                                    Cocklebur 2     0     2   2   2   1       0                                    Crabgrass 3     0     2   3   3   2       1                                    Downy brome                                                                              1     0     1   1   1   0       0                                    Giant Foxtail                                                                            2     0     1   2   1   1       1                                    Morningglory                                                                             6     0     3   3   2   3       1                                    Sorghum   2     0     2   2   1   0       1                                    Velvetleaf                                                                               2     0     1   1   2   0       1                                    Wild Oat  1     0     0   1   2   0       0                                    ______________________________________                                    

TEST B

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarter (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza saliva), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (--) response means no test result.

                  TABLE B                                                          ______________________________________                                                           Compound                                                     Rate 2000 g/ha      68    71                                                   ______________________________________                                         POSTEMERGENCE                                                                  Barley              4     0                                                    Barnyardgrass       9     0                                                    Bedstraw            7     0                                                    Blackgrass          4     0                                                    Chickweed           6     0                                                    Cocklebur           7     0                                                    Corn                3     0                                                    Cotton              8     1                                                    Crabgrass           8     0                                                    Downy brome         3     0                                                    Giant foxtail       5     0                                                    Lambsquarter        7     --                                                   Morningglory        8     1                                                    Nutsedge            2     0                                                    Rape                9     0                                                    Rice                2     0                                                    Sorghum             2     0                                                    Soybean             5     2                                                    Sugar beet          9     0                                                    Velvetleaf          3     0                                                    Wheat               4     0                                                    Wild buckwheat      6     0                                                    Wild oat            3     0                                                    PREEMERGENCE                                                                   Barley              5     0                                                    Barnyardgrass       9     0                                                    Bedstraw            6     0                                                    Blackgrass          8     0                                                    Chickweed           8     0                                                    Cocklebur           4     0                                                    Corn                2     0                                                    Cotton              0     6                                                    Crabgrass           10    0                                                    Downy brome         7     0                                                    Giant foxtail       10    0                                                    Lambsquarter        9     --                                                   Morningglory        3     1                                                    Nutsedge            0     0                                                    Rape                9     0                                                    Rice                1     0                                                    Sorghum             2     0                                                    Soybean             0     0                                                    Sugar beet          9     0                                                    Velvetleaf          6     0                                                    Wheat               3     0                                                    Wild buckwheat      7     0                                                    Wild oat            8     0                                                    ______________________________________                                    

                                      TABLE B                                      __________________________________________________________________________     POSTEMERGENCE                                                                  Rate                                                                           1000 COMPOUND                                                                  g/ha 1 2 3 4 5 6 9 11                                                                               12                                                                               13                                                                               14                                                                               15                                                                               16                                                                               17                                                                               18                                                                               19                                                                               20                                                                               22                                                                               23                                                                               24                                                                               25                                                                               26                                                                               27                                                                               28                                                                               30                                                                               31                                                                               32                                                                               33                                                                               34                __________________________________________________________________________     Barley                                                                              8 5 6 3 8 6 3 3 5 4 5 3 2 4 3 3 3 2       8                                                                              3                                                                              7                                                                              5 2 3 3 5      2                                                                       3      3                Barn-                                                                               9 9 9 8 9 8 9 1 8 6 9 8 7 6 8 8 5 3       9                                                                              9                                                                              9                                                                              9 3 9 9 8      3                                                                       3      3                yard-                                                                          grass                                                                          Bedstraw                                                                            9 9 8 8 8 8 8 3 6 8 8 9 7 6 7 7 5 6       8                                                                              7                                                                              8                                                                              8 4 5 6 8      4                                                                       7      3                Black-                                                                              9 9 7 6 9 8 6 2 6 5 9 6 4 8 5 3 2 2       9                                                                              5                                                                              9                                                                              8 4 8 8 7      2                                                                       5      2                grass                                                                          Chick-                                                                              9 8 7 9 9 6 7 2 8 7 9 7 6 8 6 4 3 4       9                                                                              8                                                                              9                                                                              9 3 6 7 8      3                                                                       6      2                weed                                                                           Cockle-                                                                             7 7 8 8 9 8 6 6 8 6 7 8 6 8 7 8 5 3       8                                                                              8                                                                              9                                                                              6 5 7 6 5      3                                                                       6      3                bur                                                                            Corn 8 5 6 2 8 6 3 2 3 3 7 3 4 6 4 3 3 2       5                                                                              2                                                                              6                                                                              3 2 5 3 3      2                                                                       3      1                Cotton                                                                              10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 9 9 8 8 9 9 9 10                                                                               9 4       10                                                                             8                                                                              10                                                                             9 9 9 7 9      9                                                                       6      0                Crab-                                                                               9 9 9 8 9 8 7 2 8 6 8 8 3 8 8 9 9 3       9                                                                              8                                                                              9                                                                              9 3 9 6 8      3                                                                       4      4                grass                                                                          Downy                                                                               8 6 3 5 9 6 5 1 5 4 9 5 3 8 2 2 3 2       9                                                                              3                                                                              8                                                                              5 2 4 1 5      1                                                                       3      1                brome                                                                          Giant                                                                               9 9 9 7 9 8 3 1 6 3 9 7 3 8 7 5 4 2       9                                                                              2                                                                              9                                                                              7 3 8 6 5      2                                                                       2      3                foxtail                                                                        Lambs-                                                                              8 10                                                                               9 8 7 8 8 2 9 8 4 9 8 5 6 5 5 7       6                                                                              8                                                                              7                                                                              8 7 5 7 7      6                                                                       7      1                quarter                                                                        Morn-                                                                               9 9 5 9 8 8 6 3 9 7 6 9 3 6 7 6 7 3       8                                                                              8                                                                              8                                                                              8 7 5 7 6      6                                                                       4      4                ing-                                                                           glory                                                                          Nut- 7 5 3 1 7 5 1 1 3 1 1 0 1 1 3 2 2 0       2                                                                              2                                                                              7                                                                              3 3 5 1 1      0                                                                       0      0                sedge                                                                          Rape 9 9 9 9 9 9 8 5 9 8 9 8 7 8 6 7 8 8       10                                                                             8                                                                              9                                                                              9 6 9 8 8      6                                                                       9      8                Rice 6 5 5 2 4 3 3 2 3 2 3 3 1 3 4 3 3 1       4                                                                              2                                                                              5                                                                              4 4 3 1 3      3                                                                       3      0                Sorghum                                                                             8 5 7 5 7 4 4 1 3 3 3 3 1 3 5 2 2 1       9                                                                              3                                                                              5                                                                              4 3 4 2 6      2                                                                       3      1                Soybean                                                                             5 7 9 9 2 6 6 1 2 5 2 6 6 5 7 5 6 5       4                                                                              5                                                                              6                                                                              6 4 3 8 7      4                                                                       4      2                Sugar                                                                               8 10                                                                               9 9 10                                                                               10                                                                               8 7 10                                                                               7 10                                                                               9 9 9 10                                                                               10                                                                               9 8       10                                                                             9                                                                              9                                                                              10                                                                               8 6 9 9      8                                                                       9      2                beet                                                                           Velvet                                                                              8 8 9 8 8 8 4 2 6 3 6 8 4 6 9 8 6 2       8                                                                              3                                                                              9                                                                              8 4 4 6 8      5                                                                       4      3                leaf                                                                           Wheat                                                                               8 4 4 4 7 4 2 2 2 4 5 4 3 4 2 2 2 2       7                                                                              3                                                                              7                                                                              5 1 4 4 5      1                                                                       3      2                Wild 9 9 8 8 9 3 7 3 9 8 9 8 5 9 3 6 4 4       9                                                                              7                                                                              9                                                                              9 3 4 6 9      5                                                                       7      2                buck-                                                                          wheat                                                                          Wild oat                                                                            9 6 7 6 9 8 6 1 4 5 9 6 3 7 3 3 2 2       9                                                                              4                                                                              9                                                                              8 2 5 6 7      1                                                                       2      1                __________________________________________________________________________     Rate 1000 g/ha                                                                          35                                                                               36                                                                               37                                                                               38                                                                               39                                                                               40                                                                               41                                                                               42                                                                               43                                                                               44                                                                               45                                                                               46                                                                               47                                                                               48                                                                               49                                                                               50                                                                               51                                                                               52                                                                               53                                                                               54                                                                               55                                                                               56 57 58 59                 __________________________________________________________________________     Barley   2 4 5 4 5 3 4 1 3 1 2 9 8 4 3 3 1 4       2                                                                              6                                                                              3                                                                              7  2                        Barnyardgrass                                                                           2 3 8 8 8 4 8 2 7 2 4 9 9 1 9 7 3 9       3                                                                              9                                                                              7                                                                              9  7  9  2                  Bedstraw 4 5 6 8 6 6 9 2 8 6 4 9 9 7 3 7 3 5       4                                                                              3                                                                              6                                                                              6  4  8  4                  Blackgrass                                                                              1 3 7 5 6 3 6 1 5 3 2 10                                                                               9 8 8 4 2 8       2                                                                              7                                                                              5                                                                              6  4  3  2                  Chickweed                                                                               3 6 6 7 6 8 8 3 7 5 6 9 9 9 7 6 2 9       4                                                                              6                                                                              8                                                                              8  6  5  3                  Cocklebur                                                                               2 6 4 5 4 6 3 2 5 5 3 8 7 4 6 6 2 7       8                                                                              7                                                                              6                                                                              8  6  3  5                  Corn     2 2 8 3 8 3 7 2 6 1 3 8 6 1 7 3 1 8       3                                                                              4                                                                              2                                                                              6  2  7  1                  Cotton   2 8 8 9 7 8 8 3 9 7 3 5 10                                                                               8 9 9 2 9       10                                                                             5                                                                              9                                                                              8  9  9  9                  Crabgrass                                                                               2 3 8 6 7 4 7 1 7 2 3 9 9 6 9 3 2 8       3                                                                              9                                                                              3                                                                              9  7  4  2                  Downy brome                                                                             0 2 7 4 6 2 4 0 4 2 1 8 6 3 6 3 1 5       1                                                                              3                                                                              2                                                                              5  2  1  1                  Giant foxtail                                                                           1 2 8 7 7 3 7 1 6 2 3 9 9 4 9 4 1 8       3                                                                              9                                                                              4                                                                              9  7  6  2                  Lambsquarter                                                                            4 6 1 6 3 5 7 3 3 6 7 8 9 5 6 6 4 10      8                                                                              8                                                                              7                                                                              8  6  6  5                  Morningglory                                                                            6 6 4 4 3 6 6 4 6 4 7 8 9 6 7 8 2 8       9                                                                              8                                                                              3                                                                              9  4  6  6                  Nutsedge 0 0 7 1 1 2 1 0 0 1 --                                                                               --                                                                               5 --                                                                               0 0 0 3       2                                                                              2                                                                              0                                                                              7  1  4  0                  Rape     4 8 9 9 8 6 8 1 5 6 4 10                                                                               10                                                                               10                                                                               6 8 2 9       5                                                                              6                                                                              7                                                                              8  9  6                     Rice     1 1 2 3 2 3 1 1 3 3 1 5 7 3 2 3 0 5       2                                                                              3                                                                              2                                                                              6  2  3  1                  Sorghum  1 2 3 2 3 2 3 0 2 2 2 8 8 2 6 2 1 5       3                                                                              5                                                                              2                                                                              7  3  6  1                  Soybean  3 3 2 6 3 5 7 3 7 5 4 3 9 2 5 7 1 6       4                                                                              6                                                                              5                                                                              8  6  9  4                  Sugar beet                                                                              7 8 1 10                                                                               3 9 9 7 5 9 6 9 9 8 9 9 4 10      9                                                                              9                                                                              8                                                                              9  9  9  8                  Velvetleaf                                                                              1 2 3 4 2 4 7 3 5 2 6 8 8 2 4 5 1 8       3                                                                              7                                                                              2                                                                              7  2  2  2                  Wheat    1 3 6 3 6 3 5 1 3 2 3 9 9 5 3 3 2 4       0                                                                              3                                                                              2                                                                              3  3  6  2                  Wild buckwheat                                                                          5 6 7 5 9 2 9 2 2 7 3 8 9 5 3 6 2 10      9                                                                              6                                                                              5                                                                              8  3  6  5                  Wild oat 1 2 7 4 6 2 5 0 2 2 4 10                                                                               10                                                                               7 8 4 1 7       1                                                                              6                                                                              3                                                                              8  5  8  3                  __________________________________________________________________________     PRE-EMERGENCE                                                                  Rate                                                                           1000                                                                           g/ha 1 2 3 4 5 6 9 11                                                                               12                                                                               13                                                                               14                                                                               15                                                                               16                                                                               17                                                                               18                                                                               19                                                                               20                                                                               22      23                                                                             24                                                                             25                                                                             26                                                                               27                                                                               28                                                                               30                                                                               31     32                                                                      33     34               __________________________________________________________________________     Barley                                                                              10                                                                               5 8 8 7 4 5 0 5 5 9 6 8 6 3 5 2 1       9                                                                              7                                                                              9                                                                              8 0 3 6 3      1                                                                       0      0                Barn-                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 9 9 1 9 9 9 9 9 8 9 9 7 6       10                                                                             9                                                                              9                                                                              9 3 7 9 10     4                                                                       9      4                yard-                                                                          grass                                                                          Bedstraw                                                                            7 8 8 9 8 9 5 3 7 6 9 8 9 9 9 10                                                                               6 1       7                                                                              6                                                                              8                                                                              6 2 2 7 5      2                                                                       --     0                Black-                                                                              9 10                                                                               10                                                                               10                                                                               9 9 9 0 10                                                                               9 9 9 9 8 10                                                                               9 6 8       10                                                                             10                                                                             10                                                                             10                                                                               4 7 8 7      2                                                                       7      2                grass                                                                          Chick-                                                                              9 9 9 9 10                                                                               9 9 0 10                                                                               9 10                                                                               9 9 9 9 10                                                                               5 5       9                                                                              9                                                                              10                                                                             9 4 8 9 9      7                                                                       --     7                weed                                                                           Cockle-                                                                             4 3 4 1 3 2 1 1 1 1 0 0 0 0 2 1 1 0       4                                                                              2                                                                              3                                                                              4 3 0 0 3      0                                                                       0      0                bur                                                                            Corn 9 6 7 2 5 4 5 0 3 4 5 2 3 3 4 2 0 0       8                                                                              3                                                                              7                                                                              4 0 6 6 3      1                                                                       2      1                Cotton                                                                              7 2 1 9 6 1 2 2 1 2 3 0 0 3 1 2 2 0       3                                                                              2                                                                              4                                                                              1 0 0 0 2      0                                                                       0      0                Crab-                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               1 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9       10                                                                             10                                                                             10                                                                             10                                                                               7 10                                                                               10                                                                               9      7                                                                       9      8                grass                                                                          Downy                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 0 10                                                                               9 10                                                                               9 8 10                                                                               8 10                                                                               3 3       10                                                                             9                                                                              10                                                                             9 2 4 8 7      2                                                                       --     0                brome                                                                          Giant                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               2 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 9       10                                                                             10                                                                             10                                                                             10                                                                               5 9 10                                                                               10     3                                                                       6      9                foxtail                                                                        Lambs-                                                                              10                                                                               10                                                                               9 10                                                                               9 10                                                                               9 0 9 9 10                                                                               10                                                                               10                                                                               9 9 9 7 4       9                                                                              8                                                                              10                                                                             9 4 5 10                                                                               9      7                                                                       --     6                quarter                                                                        Morn-                                                                               9 9 9 8 9 9 7 0 7 4 9 7 3 3 3 2 2 2       9                                                                              8                                                                              9                                                                              9 2 2 5 5      5                                                                       6      0                ing                                                                            glory                                                                          Nuts-                                                                               5 3 5 0 --                                                                               --                                                                               0 --                                                                               --                                                                               1 2 1 0 0 0 0 0 --      3                                                                              0                                                                              0                                                                              0 0 0 0 0      0                                                                       0      0                edge                                                                           Rape 10                                                                               9 10                                                                               10                                                                               6 8 8 0 8 8 9 9 10                                                                               9 8 9 2 4       10                                                                             8                                                                              10                                                                             7 5 9 8 8      3                                                                       3      6                Rice 2 1 2 1 0 1 1 0 0 1 0 0 1 0 0 0 0 5       3                                                                              1                                                                              1                                                                              4 2 0 2 1      2                                                                       2      0                Sorghum                                                                             9 7 8 2 2 3 6 1 3 4 4 3 3 3 2 3 2 0       8                                                                              6                                                                              6                                                                              4 0 3 3 7      1                                                                       2      0                Soybean                                                                             0 6 4 6 1 2 1 0 1 0 0 0 2 0 1 3 1 0       2                                                                              2                                                                              1                                                                              3 0 1 4 1      2                                                                       1      0                Sugar                                                                               10                                                                               10                                                                               9 9 10                                                                               9 9 1 9 9 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 6       10                                                                             9                                                                              10                                                                             9 5 4 9 9      8                                                                       --     3                beet                                                                           Velvet                                                                              10                                                                               9 10                                                                               10                                                                               10                                                                               7 7 0 9 6 10                                                                               10                                                                               7 7 7 7 7 5       10                                                                             6                                                                              10                                                                             6 3 8 9 7      3                                                                       9      0                leaf                                                                           Wheat                                                                               9 6 9 5 8 6 3 0 3 6 9 6 8 6 1 5 1 2       9                                                                              3                                                                              9                                                                              6 0 5 8 3      1                                                                       1      0                Wild 9 6 8 10                                                                               10                                                                               2 7 2 8 7 9 7 5 9 3 3 2 1       9                                                                              5                                                                              7                                                                              7 1 9 6 4      1                                                                       --     2                buck-                                                                          wheat                                                                          Wild 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 9 2 10                                                                               9 10                                                                               9 9 9 8 9 7 3       10                                                                             9                                                                              10                                                                             9 3 8 9 8      1                                                                       5      2                oat                                                                            __________________________________________________________________________     Rate 1000 g/ha                                                                          35                                                                               36                                                                               37                                                                               38                                                                               39                                                                               40                                                                               41                                                                               42                                                                               43                                                                               44                                                                               45                                                                               46                                                                               47                                                                               48                                                                               49                                                                               50                                                                               51                                                                               52                                                                               53                                                                               54                                                                               55                                                                               56 57 58 59                 __________________________________________________________________________     Barley   0 4 4 3 2 3 2 0 1 1 0 8 7 2 1 2 0 3       1                                                                              7                                                                              4                                                                              9  3  1  1                  Barnyardgrass                                                                           3 8 9 9 7 9 9 2 8 2 8 10                                                                               10                                                                               3 10                                                                               9 7 10      6                                                                              10                                                                             9                                                                              10 9  10 5                  Bedstraw 0 6 1 5 6 2 3 1 7 1 2 9 10                                                                               3 4 4 3 8       0                                                                              1                                                                              9                                                                              8  8  9  5                  Blackgrass                                                                              2 6 7 9 6 5 4 0 4 3 1 10                                                                               10                                                                               9 10                                                                               9 4 10      3                                                                              9                                                                              9                                                                              10 9  10 3                  Chickweed                                                                               3 9 9 10                                                                               10                                                                               9 10                                                                               5 6 4 1 10                                                                               9 9 10                                                                               9 7 10      6                                                                              9                                                                              9                                                                              9  8  9  8                  Cocklebur                                                                               0 0 0 1 0 1 0 0 0 0 0 5 6 0 2 1 0 5       0                                                                              1                                                                              2                                                                              3  1  1  1                  Corn     0 0 7 4 7 3 2 0 2 3 1 5 8 0 6 3 2 8       1                                                                              4                                                                              3                                                                              5  2  6  1                  Cotton   0 1 0 0 1 1 3 2 0 2 1 6 3 6 0 0 1 2       0                                                                              0                                                                              4                                                                              8  2  0  0                  Crabgrass                                                                               9 9 10                                                                               10                                                                               9 10                                                                               10                                                                               9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               7 10                                                                               10                                                                               8 10      7                                                                              10                                                                             10                                                                             10 10 10 9                  Downy brome                                                                             1 4 10                                                                               10                                                                               7 6 4 0 3 2 0 10                                                                               10                                                                               7 9 5 1 10      1                                                                              10                                                                             10                                                                             10 10 4  3                  Giant foxtail                                                                           9 7 10                                                                               10                                                                               9 9 10                                                                               7 10                                                                               6 10                                                                               10                                                                               10                                                                               7 10                                                                               10                                                                               9 10      5                                                                              10                                                                             9                                                                              10 10 10 3                  Lambsquarter                                                                            4 9 1 9 10                                                                               9 9 9 5 5 7 10                                                                               10                                                                               10                                                                               10                                                                               9 1 10      10                                                                             10                                                                             9                                                                              10 9  9  8                  Morningglory                                                                            1 3 1 4 3 6 7 2 2 1 1 10                                                                               10                                                                               4 8 6 1 10      0                                                                              10                                                                             6                                                                              9  6  8  4                  Nutsedge 0 0 1 9 2 1 1 0 0 0 0 --                                                                               --                                                                               --                                                                               0 0 0 1       0                                                                              --                                                                             0                                                                              -- 0  1  0                  Rape     2 5 9 9 7 3 7 1 7 0 1 10                                                                               10                                                                               10                                                                               9 9 2 10      2                                                                              9                                                                              10                                                                             10 10 9  5                  Rice     0 0 2 0 2 0 1 0 0 1 0 5 5 0 4 1 0 3       2                                                                              4                                                                              1                                                                              2  0  2  0                  Sorghum  0 0 5 1 3 2 3 0 0 1 0 8 9 0 5 4 0 5       0                                                                              8                                                                              2                                                                              8  1  5  1                  Soybean  0 1 1 0 1 1 0 0 0 0 4 5 9 1 3 0 1 2       1                                                                              4                                                                              4                                                                              4  2  6  1                  Sugar beet                                                                              3 8 0 10                                                                               7 9 8 7 8 8 2 10                                                                               10                                                                               9 9 7 3 10      4                                                                              10                                                                             9                                                                              10 9  10 9                  Velvetleaf                                                                              0 3 4 6 1 6 8 2 10                                                                               3 1 10                                                                               7 1 9 3 1 10      0                                                                              8                                                                              9                                                                              9  6  5  4                  Wheat    0 4 6 5 5 5 5 0 2 3 0 9 8 3 8 1 0 4       0                                                                              5                                                                              6                                                                              9  5  2  2                  Wild buckwheat                                                                          0 5 3 5 9 2 3 0 0 2 1 10                                                                               10                                                                               4 9 3 2 6       2                                                                              5                                                                              8                                                                              10 9  7  6                  Wild oat 1 8 9 9 9 9 9 0 8 6 0 10                                                                               10                                                                               5 10                                                                               9 4 10      4                                                                              10                                                                             9                                                                              10 8  9  6                  __________________________________________________________________________

                  TABLE B                                                          ______________________________________                                                   COMPOUND                                                             Rate 400 g/ha                                                                              7      10     21   51   68   70   71                               ______________________________________                                         POSTEMERGENCE                                                                  Barley      3      4      1    0    3    0    --                               Barnyardgrass                                                                              4      9      6    1    3    0    0                                Bedstraw    6      8      3    3    6    0    0                                Blackgrass  4      7      3    2    4    1    0                                Chickweed   5      6      4    1    5    0    0                                Cocklebur   7      4      2    2    5    0    0                                Corn        2      7      2    2    2    0    0                                Cotton      9      10     1    2    7    0    0                                Crabgrass   7      8      6    1    3    0    0                                Downy brome 2      5      1    0    2    0    0                                Cocklebur   7      4      2    2    5    0    0                                Corn        2      7      2    2    2    0    0                                Cotton      9      10     1    2    7    0    0                                Crabgrass   7      8      6    1    3    0    0                                Downy brome 2      5      1    0    2    0    0                                Giant foxtail                                                                              7      8      2    1    2    0    0                                Lambsquarter                                                                               9      9      7    2    6    1    0                                Morningglory                                                                               8      8      7    2    4    0    1                                Nutsedge    1      8      0    0    0    0    0                                Rape        6      8      6    0    8    0    --                               Rice        2      3      1    1    2    0    0                                Sorghum     1      4      1    1    1    0    0                                Soybean     4      5      1    3    4    1    2                                Sugar beet  8      9      7    3    8    3    --                               Velvetleaf  6      9      6    2    --   0    0                                Wheat       3      4      2    0    3    0    --                               Wild buckwheat                                                                             4      5      4    1    5    1    0                                Wild oat    5      8      1    0    2    0    --                               PREEMERGENCE                                                                   Barley      4      5      1    0    2    0    0                                Barnyardgrass                                                                              9      10     8    3    4    0    0                                Bedstraw    7      10     2    0    3    3    0                                Blackgrass  9      10     8    1    4    0    0                                Chickweed   9      9      9    0    6    0    0                                Cocklebur   0      1      0    0    0    0    0                                Corn        2      6      1    1    1    0    0                                Cotton      1      1      0    0    0    0    0                                Crabgrass   9      10     10   9    9    0    0                                Downy brome 8      10     3    0    3    0    0                                Giant foxtail                                                                              10     10     10   8    8    0    0                                Lambsquarter                                                                               9      9      9    4    8    0    0                                Morningglory                                                                               7      10     4    0    4    0    0                                Nutsedge    2      10     0    0    0    0    0                                Rape        6      9      7    0    5    0    0                                Rice        1      1      1    0    0    0    0                                Sorghum     4      7      3    0    1    0    0                                Soybean     0      1      0    0    0    0    0                                Sugar beet  10     10     10   2    8    0    0                                Velvetleaf  7      9      4    0    2    0    0                                Wheat       4      4      0    0    0    0    0                                Wild buckwheat                                                                             4      8      7    0    1    1    0                                Wild oat    9      9      5    0    6    0    0                                ______________________________________                                    

                                      TABLE B                                      __________________________________________________________________________     POSTEMERGENCE                                                                  Rate 200                                                                            COMPOUND                                                                  g/ha 1 2 3 4 5 6 9 11                                                                               12                                                                               13                                                                               14                                                                               15                                                                               16                                                                               17                                                                               18                                                                               19                                                                               20                                                                               22                                                                               23                                                                               24                                                                               25                                                                               26                                                                               27                                                                               28                                                                               30                                                                               31                                                                               32                                                                               33                                                                               34                __________________________________________________________________________     Barley                                                                              7 3 3 2 5 3 3 1 2 3 3 3 2 3 2 3 2 0       6                                                                              3                                                                              5                                                                              3 1 1 3 4      2                                                                       1      1                Barn-                                                                               9 9 9 3 8 4 6 0 3 3 5 3 2 3 3 3 2 0       8                                                                              7                                                                              9                                                                              6 2 6 3 4      2                                                                       3      1                yard-                                                                          grass                                                                          Bedstraw                                                                            7 8 8 4 6 6 7 2 2 6 6 6 7 5 6 7 6 4       7                                                                              7                                                                              8                                                                              7 3 2 5 7      3                                                                       4      1                Black-                                                                              9 4 4 2 6 2 4 0 3 3 6 4 3 5 2 3 2 2       7                                                                              4                                                                              8                                                                              4 2 5 3 5      1                                                                       3      1                grass                                                                          Chick-                                                                              9 7 4 7 7 6 4 2 4 5 7 5 5 6 3 3 3 3       8                                                                              6                                                                              8                                                                              7 2 3 3 7      2                                                                       3      1                weed                                                                           Cockle-                                                                             4 6 6 5 7 6 5 2 3 4 4 6 6 6 6 5 5 2       5                                                                              7                                                                              8                                                                              6 4 5 6 5      3                                                                       4      1                bur                                                                            Corn 6 4 4 2 6 4 2 0 3 2 3 2 2 1 2 2 1 2       3                                                                              2                                                                              4                                                                              3 2 3 2 2      2                                                                       3      0                Cotton                                                                              9 9 9 9 9 9 9 4 6 8 6 5 8 7 9 9 9 1       9                                                                              9                                                                              10                                                                             9 9 4 6 8      9                                                                       7      0                Crab-                                                                               8 9 9 6 6 4 4 1 5 3 7 3 2 5 5 8 3 --      9                                                                              6                                                                              9                                                                              6 3 6 3 4      3                                                                       3      1                grass                                                                          Downy                                                                               7 3 2 2 3 1 3 1 2 3 6 3 2 4 1 2 2 0       6                                                                              3                                                                              7                                                                              3 0 1 1 5      1                                                                       2      0                brome                                                                          Giant                                                                               8 7 8 3 6 3 2 1 3 2 6 2 1 3 3 5 1 0       7                                                                              3                                                                              9                                                                              3 2 4 4 3      1                                                                       1      0                foxtail                                                                        Lambs-                                                                              6 10                                                                               9 8 2 7 5 0 8 5 3 7 7 4 4 3 3 5       4                                                                              8                                                                              6                                                                              7 4 1 6 6      3                                                                       4      0                quarter                                                                        Morning-                                                                            7 8 3 8 7 8 --                                                                               1 5 2 6 8 4 4 6 6 7 2       8                                                                              4                                                                              8                                                                              8 3 3 7 5      5                                                                       4      2                glory                                                                          Nutsedge                                                                            4 1 1 0 3 0 0 0 2 0 0 0 0 0 0 0 0 0       2                                                                              0                                                                              5                                                                              0 0 2 0 0      0                                                                       0      0                Rape 9 9 9 9 6 6 8 2 5 4 7 8 7 8 3 7 2 4       9                                                                              8                                                                              8                                                                              9 4 8 7 7      4                                                                       5      4                Rice 3 3 3 1 2 3 2 0 2 2 1 3 1 1 1 0 1 0       3                                                                              2                                                                              3                                                                              4 3 1 1 2      2                                                                       3      0                Sorghum                                                                             6 5 3 1 2 1 2 0 1 2 2 2 1 1 3 1 1 0       6                                                                              1                                                                              5                                                                              3 3 1 --                                                                               4      1                                                                       3      0                Soybean                                                                             3 7 8 7 3 3 6 1 2 4 2 5 5 2 5 3 4 4       3                                                                              6                                                                              5                                                                              5 4 2 7 3      5                                                                       5      0                Sugar                                                                               8 10                                                                               9 8 10                                                                               10                                                                               8 3 10                                                                               6 7 9 9 8 8 8 8 7       9                                                                              8                                                                              9                                                                              9 7 2 8 5      5                                                                       4      0                beet                                                                           Velvet-                                                                             6 8 3 6 7 3 3 2 3 2 4 5 2 2 7 4 3 2       8                                                                              --                                                                             8                                                                              7 3 2 4 4      5                                                                       3      3                leaf                                                                           Wheat                                                                               7 2 2 3 5 2 2 1 1 2 3 3 2 3 1 2 2 1       5                                                                              3                                                                              6                                                                              2 0 1 2 2      0                                                                       2      1                Wild 9 7 5 7 6 1 8 3 2 7 7 6 4 8 3 4 3 3       9                                                                              5                                                                              8                                                                              7 3 2 6 8      4                                                                       5      2                buck-                                                                          wheat                                                                          Wild oat                                                                            8 2 3 3 4 2 5 1 3 2 5 3 3 4 1 2 1 1       7                                                                              4                                                                              6                                                                              3 1 3 4 3      0                                                                       1      1                __________________________________________________________________________             Rate 200                                                                            COMPOUND                                                                  g/ha 35                                                                               36                                                                               37                                                                               38                                                                               39                                                                               40                                                                               41                                                                               42                                                                               43                                                                               44                                                                               45                                                                               52                                                                               53                                                                               54                                                                               55                                                                               56                                                                               57                                                                               58                                                                               59                                                                               60                                                                               61                                                                               62                                                                               63                                                                               64                                                                               65                __________________________________________________________________________             Barley                                                                              1 3 1 3 2 2 1 1 2 2 0 6 6 2 1 3 0 2       0                                                                              2                                                                              2                                                                              3 3 3 1                         Barn-                                                                               0 2 4 2 4 2 5 2 3 2 1 7 9 1 6 3 2 7       3                                                                              9                                                                              3                                                                              8 3 2 2                         yard-                                                                          grass                                                                          Bedstraw                                                                            1 4 3 6 5 6 6 3 6 5 4 7 9 3 2 7 2 3       3                                                                              2                                                                              7                                                                              3 4 6 3                         Black-                                                                              0 2 2 2 3 2 3 1 2 3 1 7 9 2 6 2 1 7       1                                                                              6                                                                              2                                                                              2 2 1 2                         grass                                                                          Chick-                                                                              2 3 3 5 5 5 6 2 4 3 2 9 9 4 5 3 2 6       3                                                                              3                                                                              7                                                                              5 5 3 3                         weed                                                                           Cockle-                                                                             2 4 2 5 2 3 3 1 2 3 2 6 6 2 5 3 2 4       6                                                                              7                                                                              6                                                                              7 4 4 3                         bur                                                                            Corn 1 2 6 2 4 1 3 1 2 1 1 7 5 1 3 2 1 4       3                                                                              3                                                                              1                                                                              4 2 1 1                         Cotton                                                                              1 9 3 5 7 8 7 3 4 7 2 2 4 6 4 5 1 9       4                                                                              6                                                                              9                                                                              4 10                                                                               2 9                         Crab-                                                                               1 2 6 1 2 2 3 1 2 2 2 5 7 2 5 1 2 5       3                                                                              6                                                                              2                                                                              9 3 4 2                         grass                                                                          Downy                                                                               0 1 1 2 4 2 2 0 0 1 0 3 3 1 2 1 1 2       2                                                                              2                                                                              2                                                                              2 0 1 0                         brome                                                                          Giant                                                                               1 1 4 2 2 2 2 1 2 2 1 8 9 2 5 1 1 5       2                                                                              6                                                                              3                                                                              9 2 3 2                         foxtail                                                                        Lambs-                                                                              2 4 1 4 0 4 5 2 1 5 4 4 7 1 4 6 3 8       3                                                                              6                                                                              6                                                                              8 6 5 5                         quarter                                                                        Morning-                                                                            2 2 2 2 2 2 6 2 2 4 1 7 8 3 5 5 1 7       6                                                                              7                                                                              --                                                                             8 --                                                                               2 3                         glory                                                                          Nutsedge                                                                            0 0 2 0 0 0 0 0 0 0 --                                                                               3 1 0 0 0 0 0       0                                                                              1                                                                              0                                                                              2 0 0 0                         Rape 4 6 7 7 5 4 3 1 2 6 1 7 8 3 4 5 2 3       6                                                                              3                                                                              7                                                                              4 7 7 6                         Rice 1 2 0 2 0 2 2 0 0 2 0 1 1 0 1 2 0 2       2                                                                              1                                                                              1                                                                              2 1 2 1                         Sorghum                                                                             0 1 1 1 0 2 1 0 1 1 1 3 3 0 1 1 0 3       3                                                                              3                                                                              1                                                                              3 1 1 1                         Soybean                                                                             2 2 0 6 2 4 7 3 5 3 2 1 9 1 3 5 2 6       3                                                                              5                                                                              5                                                                              8 4 5 3                         Sugar                                                                               5 8 1 9 0 9 6 2 2 6 2 6 8 3 7 3 4 9       2                                                                              9                                                                              9                                                                              9 8 7 8                         beet                                                                           Velvet-                                                                             1 1 2 3 1 2 2 2 3 1 2 8 7 3 3 3 0 4       3                                                                              7                                                                              1                                                                              2 2 1 1                         leaf                                                                           Wheat                                                                               0 2 2 3 3 3 2 1 2 2 1 6 5 1 1 2 1 1       0                                                                              2                                                                              2                                                                              2 2 1 2                         Wild 2 1 3 3 7 2 7 1 0 4 2 6 6 3 1 3 2 8       6                                                                              6                                                                              5                                                                              8 1 6 3                         buck-                                                                          wheat                                                                          Wild oat                                                                            0 1 0 1 2 2 1 0 1 2 0 10                                                                               6 6 3 1 1 2       0                                                                              3                                                                              3                                                                              7 3 2 1                 __________________________________________________________________________     PREEMERGENCE                                                                   Rate 200                                                                            COMPOUND                                                                  g/ha 1 2 3 4 5 6 9 11                                                                               12                                                                               13                                                                               14                                                                               15                                                                               16                                                                               17                                                                               18                                                                               19                                                                               20                                                                               22                                                                               23                                                                               24                                                                               25                                                                               26                                                                               27                                                                               28                                                                               30                                                                               31                                                                               32                                                                               33                                                                               34                __________________________________________________________________________     Barley                                                                              7 3 3 2 5 3 3 1 2 3 3 3 2 3 2 3 2 0       6                                                                              3                                                                              5                                                                              3 1 1 3 4      2                                                                       1      1                Barn-                                                                               9 9 9 3 8 4 6 0 3 3 5 3 2 3 3 3 2 0       8                                                                              7                                                                              9                                                                              6 2 6 3 4      2                                                                       3      1                yard-                                                                          grass                                                                          Bedstraw                                                                            7 8 8 4 6 6 7 2 2 6 6 6 7 5 6 7 6 4       7                                                                              7                                                                              8                                                                              7 3 2 5 7      3                                                                       4      1                Black-                                                                              9 4 4 2 6 2 4 0 3 3 6 4 3 5 2 3 2 2       7                                                                              4                                                                              8                                                                              4 2 5 3 5      1                                                                       3      1                grass                                                                          Chick-                                                                              9 7 4 7 7 6 4 2 4 5 7 5 5 6 3 3 3 3       8                                                                              6                                                                              8                                                                              7 2 3 3 7      2                                                                       3      1                weed                                                                           Cockle-                                                                             4 6 6 5 7 6 5 2 3 4 4 6 6 6 6 5 5 2       5                                                                              7                                                                              8                                                                              6 4 5 6 5      3                                                                       4      1                bur                                                                            Corn 6 4 4 2 6 4 2 0 3 2 3 2 2 1 2 2 1 2       3                                                                              2                                                                              4                                                                              3 2 3 2 2      2                                                                       3      0                Cotton                                                                              9 9 9 9 9 9 9 4 6 8 6 5 8 7 9 9 9 1       9                                                                              9                                                                              10                                                                             9 9 4 6 8      9                                                                       7      0                Crab-                                                                               8 9 9 6 6 4 4 1 5 3 7 3 2 5 5 8 3 --      9                                                                              6                                                                              9                                                                              6 3 6 3 4      3                                                                       3      1                grass                                                                          Downy                                                                               7 3 2 2 3 1 3 1 2 3 6 3 2 4 1 2 2 0       6                                                                              3                                                                              7                                                                              3 0 1 1 5      1                                                                       2      0                brome                                                                          Giant                                                                               8 7 8 3 6 3 2 1 3 2 6 2 1 3 3 5 1 0       7                                                                              3                                                                              9                                                                              3 2 4 4 3      1                                                                       1      0                foxtail                                                                        Lambs-                                                                              6 10                                                                               9 8 2 7 5 0 8 5 3 7 7 4 4 3 3 5       4                                                                              8                                                                              6                                                                              7 4 1 6 6      3                                                                       4      0                quarter                                                                        Morning-                                                                            7 8 3 8 7 8 --                                                                               1 5 2 6 8 4 4 6 6 7 2       8                                                                              4                                                                              8                                                                              8 3 3 7 5      5                                                                       4      2                glory                                                                          Nutsedge                                                                            4 1 1 0 3 0 0 0 2 0 0 0 0 0 0 0 0 0       2                                                                              0                                                                              5                                                                              0 0 2 0 0      0                                                                       0      0                Rape 9 9 9 9 6 6 8 2 5 4 7 8 7 8 3 7 2 4       9                                                                              8                                                                              8                                                                              9 4 8 7 7      4                                                                       5      4                Rice 3 3 3 1 2 3 2 0 2 2 1 3 1 1 1 0 1 0       3                                                                              2                                                                              3                                                                              4 3 1 1 2      2                                                                       3      0                Sorghum                                                                             6 5 3 1 2 1 2 0 1 2 2 2 1 1 3 1 1 0       6                                                                              1                                                                              5                                                                              3 3 1 --                                                                               4      1                                                                       3      0                Soybean                                                                             3 7 8 7 3 3 6 1 2 4 2 5 5 2 5 3 4 4       3                                                                              6                                                                              5                                                                              5 4 2 7 3      5                                                                       5      0                Sugar                                                                               8 10                                                                               9 8 10                                                                               10                                                                               8 3 10                                                                               6 7 9 9 8 8 8 8 7       9                                                                              8                                                                              9                                                                              9 7 2 8 5      5                                                                       4      0                beet                                                                           Velvet-                                                                             6 8 3 6 7 3 3 2 3 2 4 5 2 2 7 4 3 2       8                                                                              --                                                                             8                                                                              7 3 2 4 4      5                                                                       3      3                leaf                                                                           Wheat                                                                               7 2 2 3 5 2 2 1 1 2 3 3 2 3 1 2 2 1       5                                                                              3                                                                              6                                                                              2 0 1 2 2      0                                                                       2      1                Wild 9 7 5 9 6 1 8 3 2 7 7 6 4 8 3 4 3 3       9                                                                              5                                                                              8                                                                              7 3 2 6 8      4                                                                       5      2                buck-                                                                          wheat                                                                          Wild oat                                                                            8 2 3 3 4 2 5 1 3 2 5 3 3 4 1 2 1 1       7                                                                              4                                                                              6                                                                              3 1 3 4 3      0                                                                       1      1                __________________________________________________________________________             Rate 200                                                                            COMPOUND                                                                  g/ha 35                                                                               36                                                                               37                                                                               38                                                                               39                                                                               40                                                                               41                                                                               42                                                                               43                                                                               44                                                                               45                                                                               52                                                                               53                                                                               54                                                                               55                                                                               56                                                                               57                                                                               58                                                                               59                                                                               60                                                                               61                                                                               62                                                                               63                                                                               64                                                                               65                __________________________________________________________________________             Barley                                                                              0 2 1 1 0 0 0 0 2 0 0 5 3 0 0 0 0 1       0                                                                              2                                                                              1                                                                              4 0 2 0                         Barn-                                                                               0 2 5 3 4 2 4 0 2 0 1 9 10                                                                               1 10                                                                               3 3 9       1                                                                              9                                                                              3                                                                              9 3 8 2                         yard-                                                                          grass                                                                          Bedstraw                                                                            0 1 1 0 1 0 2 0 0 0 1 3 10                                                                               1 1 0 1 4       0                                                                              0                                                                              7                                                                              --                                                                               3 2 3                         Black-                                                                              0 3 4 1 3 0 0 0 0 0 0 10                                                                               10                                                                               2 9 2 3 9       0                                                                              9                                                                              6                                                                              9 5 6 1                         grass                                                                          Chick-                                                                              0 5 3 7 3 4 6 0 0 1 1 9 9 6 9 4 3 10      1                                                                              9                                                                              7                                                                              9 7 8 5                         weed                                                                           Cockle-                                                                             0 0 0 0 0 0 0 0 0 0 0 0 2 0 2 0 0 2       0                                                                              1                                                                              0                                                                              1 0 0 0                         bur                                                                            Corn 0 0 4 0 2 0 1 0 1 0 0 4 5 0 6 0 0 3       0                                                                              2                                                                              1                                                                              1 2 0                           Cotton                                                                              0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0       0                                                                              0                                                                              2                                                                              5 0 0 0                         Crab-                                                                               0 5 10                                                                               9 2 5 9 3 8 1 6 10                                                                               10                                                                               1 9 6 7 10      3                                                                              10                                                                             9                                                                              10                                                                               9 9 5                         grass                                                                          Downy                                                                               0 2 4 1 2 0 2 0 0 0 0 9 8 1 3 1 1 4       1                                                                              7                                                                              4                                                                              7 4 3 1                         brome                                                                          Giant                                                                               0 2 8 8 3 6 9 2 8 2 3 10                                                                               10                                                                               2 9 4 7 9       2                                                                              10                                                                             9                                                                              10                                                                               9 10                                                                               1                         foxtail                                                                        Lambs-                                                                              0 5 1 7 1 3 5 0 0 0 1 10                                                                               10                                                                               8 10                                                                               4 2 10      2                                                                              10                                                                             9                                                                              10                                                                               8 9 6                         quarter                                                                        Morning-                                                                            0 1 0 1 0 2 4 0 2 1 1 8 9 1 6 2 0 6       0                                                                              8                                                                              4                                                                              8 2 1 3                         glory                                                                          Nutsedge                                                                            0 0 0 0 0 0 0 0 0 0 0 --                                                                               --                                                                               --                                                                               0 0 0 0       0                                                                              --                                                                             0                                                                              --                                                                               0 0 0                         Rape 0 0 3 2 1 0 0 0 1 0 1 10                                                                               10                                                                               1 8 5 1 7       0                                                                              6                                                                              7                                                                              8 7 6 3                         Rice 0 0 0 0 0 0 0 0 0 0 0 1 2 0 1 0 0 0       1                                                                              1                                                                              0                                                                              1 0 1 0                         Sorghum                                                                             0 0 0 0 0 0 0 1 0 0 0 5 6 0 3 1 0 2       0                                                                              3                                                                              1                                                                              4 1 1 0                         Soybean                                                                             0 0 0 0 0 0 0 0 0 0 1 0 5 1 0 0 0 0       1                                                                              9                                                                              1                                                                              2 1 0 0                         Sugar                                                                               0 6 1 2 3 2 1 2 2 0 2 9 10                                                                               2 10                                                                               2 2 10      0                                                                              9                                                                              9                                                                              10                                                                               7 9 7                         beet                                                                           Velvet-                                                                             0 0 0 2 0 1 5 0 4 0 0 10                                                                               6 0 3 1 0 7       0                                                                              4                                                                              4                                                                              4 5 1 2                         leaf                                                                           Wheat                                                                               0 1 2 1 1 1 2 0 1 0 0 5 5 1 0 0 0 2       0                                                                              1                                                                              1                                                                              3 1 0 0                         Wild 0 1 1 1 3 1 1 0 0 1 1 8 8 1 3 0 1 4       0                                                                              1                                                                              4                                                                              3 4 1 2                         buck-                                                                          wheat                                                                          Wild oat                                                                            0 3 5 4 4 3 3 0 3 0 0 10                                                                               10                                                                               1 7 3 1 9       0                                                                              9                                                                              4                                                                              10                                                                               5 3 2                 __________________________________________________________________________

                  TABLE B                                                          ______________________________________                                         POSTEMERGENCE                                                                             COMPOUND                                                            Rate 100 g/ha                                                                               7        10    21     51  70                                      ______________________________________                                         Barley       2        3     1      0   0                                       Barnyardgrass                                                                               2        8     2      0   0                                       Bedstraw     5        8     2      0   0                                       Blackgrass   2        3     1      0   0                                       Chickweed    3        4     2      0   0                                       Cocklebur    3        2     0      1   0                                       Corn         1        3     1      0   0                                       Cotton       8        10    0      0   0                                       Crabgrass    3        8     2      1   0                                       Downy brome  2        2     1      0   0                                       Giant foxtail                                                                               2        6     1      0   0                                       Lambsquarter 7        9     5      2   1                                       Morningglory 8        6     4      2   0                                       Nutsedge     0        1     0      0   0                                       Rape         6        6     5      0   0                                       Rice         1        1     0      0   0                                       Sorghum      1        3     1      0   0                                       Soybean      2        5     1      1   1                                       Sugar beet   7        9     5      0   1                                       Velvetleaf   3        8     2      0   0                                       Wheat        2        1     1      0   0                                       Wild buckwheat                                                                              3        2     2      0   0                                       Wild oat     1        3     0      0   0                                       ______________________________________                                         PREEMERGENCE                                                                              COMPOUND                                                            Rate 100 g/ha                                                                               7        10    21     51  70                                      ______________________________________                                         Barley       2        2     0      0   0                                       Barnyardgrass                                                                               9        10    4      0   0                                       Bedstraw     2        9     1      0   --                                      Blackgrass   8        9     3      0   0                                       Chickweed    9        9     8      0   0                                       Cocklebur    0        0     0      0   0                                       Corn         1        3     0      0   0                                       Cotton       1        0     0      0   0                                       Crabgrass    8        9     9      1   0                                       Downy brome  4        9     1      0   0                                       Giant foxtail                                                                               10       10    10     2   0                                       Lambsquarter 9        9     8      0   0                                       Morningglory 6        4     1      0   0                                       Nutsedge     --       7     0      0   0                                       Rape         3        5     1      0   0                                       Rice         0        0     0      0   0                                       Sorghum      3        6     1      0   0                                       Soybean      0        0     0      0   0                                       Sugar beet   7        9     5      0   0                                       Velvetleaf   1        7     0      0   0                                       Wheat        1        1     0      0   0                                       Wild buckwheat                                                                              4        3     2      0   0                                       Wild oat     7        9     2      0   0                                       ______________________________________                                    

TEST C

The compounds evaluated in this test were formulated in a non-phytoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), galium (Galium aparine), giant foxtail (Setaria faberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album), morningglory (lpomoea hederacea), pigweed (Amaranthus retrofiexus), rape (Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza saliva), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass (Echinochloa crus-galli) and Late watergrass (Echinocloa oryzicola) grown to the 1 and 2 leaf stage for testing.

All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table C, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (--) response means no test result.

                  TABLE C                                                          ______________________________________                                         POSTEMERGENCE                                                                                 COMPOUND                                                        Rate 1000 g/ha 64                                                              ______________________________________                                         Barley Igri    --                                                              Barnyardgrass  --                                                              Blackgrass     --                                                              Chickweed      --                                                              Cocklebur      --                                                              Corn           --                                                              Cotton         --                                                              Crabgrass      --                                                              Downy brome    --                                                              Duck salad     90                                                              Galium         --                                                              Giant foxtail  --                                                              It. rygrass    --                                                              Johnsongrass   --                                                              Lambsquarter   --                                                              Morningglory   --                                                              Rape           --                                                              Redroot pigweed                                                                               --                                                              Rice japonica  50                                                              Soybean        --                                                              Speedwell      --                                                              Sugar beet     --                                                              Umbrella sedge 90                                                              Velvetleaf     --                                                              Watergrass 2   95                                                              Wheat          --                                                              Wild buckwheat --                                                              Wild oat       --                                                              Barnyardgrass 2                                                                               95                                                              ______________________________________                                    

                                      TABLE C                                      __________________________________________________________________________     POSTEMERGENCE                                                                             COMPOUND           COMPOUND                                                    4  5  6  12 13                                                                               24 64                                                                               1  2  3  4  5  6  12 13 14 16 23                            Rate 500 g/ha      Rate 250 g/ha                                    __________________________________________________________________________     Barley Igri                                                                               35 25 35 30 --                                                                               45 --                                                                               40 30 -- 30 25 35 30 -- 14 17 23                 Barnyardgrass                                                                             30 90 90 80 --                                                                               70 --                                                                               90 80 -- 30 90 45 35 -- 45 30 80                 Blackgrass 30 85 80 55 --                                                                               50 --                                                                               70 65 -- 30 80 70 55 -- 35 25 65                 Chickweed  75 100                                                                               95 100                                                                               --                                                                               80 --                                                                               100                                                                               100                                                                               -- 75 95 70 95 -- 60 65 90                 Cocklebur  35 80 85 50 --                                                                               65 --                                                                               55 50 -- 25 60 70 50 -- 60 60 90                 Corn       20 50 35 35 --                                                                               45 --                                                                               95 30 -- 15 45 20 25 -- 25 20 80                 Cotton     40 100                                                                               -- 90 --                                                                               100                                                                               --                                                                               100                                                                               70 -- 30 95 100                                                                               80 -- 85 50 100                Crabgrass  35 95 90 95 --                                                                               100                                                                               --                                                                               95 60 -- 30 90 30 70 -- 70 60 95                 Downy brome                                                                               10 65 20 20 --                                                                               25 --                                                                               80 0  -- 10 35 0  20 -- 30 35 60                 Duck salad 10 95 25 80 0 35 80                                                                               45 55 40 10 10 10 35 0  25 20 30                 Galium     35 95 95 0  --                                                                               70 --                                                                               20 90 -- 30 95 90 0  -- 35 55 30                 Giant foxtail                                                                             25 90 90 70 --                                                                               40 --                                                                               100                                                                               50 -- 25 90 35 35 -- 90 60 95                 It. rygrass                                                                               20 80 70 40 --                                                                               25 --                                                                               90 20 -- 0  80 30 20 -- 35 15 70                 Johnsongrass                                                                              30 85 65 60 --                                                                               95 --                                                                               100                                                                               75 -- 20 85 30 35 -- 60 35 95                 Lambsquarter                                                                              70 65 80 80 --                                                                               85 --                                                                               35 95 -- 65 40 80 80 -- 20 30 15                 Morningglory                                                                              60 90 95 95 --                                                                               100                                                                               --                                                                               85 95 -- 50 90 90 85 -- 40 35 90                 Rape       90 100                                                                               90 100                                                                               --                                                                               80 --                                                                               100                                                                               95 -- 40 80 80 80 -- 55 50 100                Redroot pigweed                                                                           50 100                                                                               90 95 --                                                                               100                                                                               --                                                                               100                                                                               90 -- 50 90 90 90 -- 85 60 90                 Rice japonica                                                                             0  25 35 45 25                                                                               55 25                                                                               70 45 30 0  15 20 35 20 30 25 50                 Soybean    90 35 70 50 --                                                                               65 --                                                                               50 100                                                                               -- 60 35 30 40 -- 20 30 65                 Speedwell  95 100                                                                               100                                                                               100                                                                               --                                                                               100                                                                               --                                                                               100                                                                               100                                                                               -- 95 100                                                                               95 100                                                                               -- 95 90 100                Sugar beet 75 100                                                                               95 100                                                                               --                                                                               100                                                                               --                                                                               100                                                                               100                                                                               -- 65 100                                                                               90 100                                                                               -- 45 60 100                Umbrella sedge                                                                            35 80 90 60 0 65 60                                                                               75 95 80 30 80 80 50 0  30 45 85                 Velvetleaf 50 90 80 90 --                                                                               65 --                                                                               90 90 -- 50 90 70 80 -- 75 60 100                Watergrass 2                                                                              35 70 80 65 40                                                                               70 85                                                                               90 65 70 30 60 65 55 40 55 30 90                 Wheat      40 40 25 15 --                                                                               25 --                                                                               65 30 -- 35 30 25 10 -- 10 15 45                 Wild buckwheat                                                                            70 90 50 55 --                                                                               55 --                                                                               80 75 -- 20 90 50 50 -- 70 85 100                Wild oat   35 40 45 35 --                                                                               40 --                                                                               85 55 -- 30 35 40 20 -- 35 30 60                 Barnyardgrass 2                                                                           25 75 85 75 20                                                                               70 90                                                                               85 95 85 25 75 70 65 15 60 40 85                 __________________________________________________________________________               COMPOUND                COMPOUND                                               24 25 26 37 55 58 62 64 1  2  3 4  5  6  7  12 13 14                 __________________________________________________________________________               Rate 250 g/ha       Rate 125 g/ha                                    __________________________________________________________________________     Barley Igri                                                                              40 45 35 35 20 25 25 -- 35 20 --                                                                               20 25 30 25 20 -- 20                 Barnyardgrass                                                                            50 85 55 60 90 50 70 -- 85 35 --                                                                               20 65 20 30 20 -- 30                 Blackgrass                                                                               35 75 35 40 70 65 65 -- 70 50 --                                                                               25 30 30 35 35 -- 30                 Chickweed 40 70 70 10 100                                                                               100                                                                               90 -- 100                                                                               100                                                                               --                                                                               75 -- -- 90 55 -- 40                 Cocklebur 50 90 80 20 35 50 40 -- 35 45 --                                                                               15 60 50 55 35 -- 55                 Corn      35 70 40 40 45 30 20 -- 60 25 --                                                                               10 35 15 25 15 -- 15                 Cotton    70 95 95 10 20 70 25 -- 95 70 --                                                                               25 95 90 65 80 -- 80                 Crabgrass 95 95 95 25 60 20 40 -- 95 40 --                                                                               25 35 15 50 50 -- 35                 Downy brome                                                                              10 65 30 0  0  0  20 -- 65 0  --                                                                               0  10 0  20 0  -- 20                 Duck salad                                                                               10 35 35 0  70 90 70 70 15 30 30                                                                               0  0  0  10 15 0  0                  Galium    70 55 45 0  65 20 0  -- 20 65 --                                                                               20 20 70 65 0  -- 20                 Giant foxtail                                                                            35 95 85 65 65 35 60 -- 100                                                                               30 --                                                                               20 85 25 30 25 -- 35                 It. rygrass                                                                              25 65 65 35 15 70 20 -- 80 20 --                                                                               0  50 30 15 10 -- 20                 Johnsongrass                                                                             55 95 90 15 35 60 60 -- 95 60 13                                                                               10 30 20 35 25 -- 35                 Lambsquarter                                                                             85 70 75 0  95 65 50 -- 15 90 --                                                                               55 0  50 35 30 -- 15                 Morningglory                                                                             65 90 90 20 40 80 75 -- 75 80 --                                                                               40 80 90 65 70 -- 40                 Rape      75 100                                                                               100                                                                               20 30 60 30 -- 95 80 --                                                                               40 45 40 25 60 -- 40                 Redroot pigweed                                                                          95 90 95 30 50 85 90 -- 70 75 --                                                                               35 85 85 80 85 -- 30                 Rice japonica                                                                            40 60 65 10 40 55 70 15 60 25 15                                                                               0  0  0  35 15 15 25                 Soybean   65 65 65 0  20 50 85 -- 30 100                                                                               --                                                                               40 35 20 50 -- -- 10                 Speedwell 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               -- -- 100                                                                               100                                                                               --                                                                               95 100                                                                               90 35 95 -- --                 Sugar beet                                                                               100                                                                               95 95 0  100                                                                               100                                                                               90 -- 100                                                                               100                                                                               --                                                                               25 95 70 100                                                                               85 -- 35                 Umbrella sedge                                                                           55 90 80 35 95 95 90 50 70 90 75                                                                               20 80 55 80 35 0  20                 Velvetleaf                                                                               65 95 90 0  30 50 30 -- 75 90 --                                                                               30 90 70 65 65 -- 45                 Watergrass 2                                                                             70 85 80 30 90 90 85 50 85 40 60                                                                               30 55 55 70 30 20 45                 Wheat     25 45 30 10 20 10 50 -- 45 25 --                                                                               25 20 20 15 0  -- 10                 Wild buckwheat                                                                           55 100                                                                               30 0  80 65 80 -- 80 35 --                                                                               0  70 50 100                                                                               45 -- 60                 Wild oat  35 85 65 35 50 70 50 -- 80 35 --                                                                               10 30 40 25 20 -- 30                 Barnyardgrass 2                                                                          70 85 70 35 95 95 85 50 80 75 70                                                                               25 65 60 50 50 0  45                 __________________________________________________________________________               COMPOUND                      COMPOUND                                         17 23 24 25 26 37 55 58 62 64 1  2  3  4  5  6  7 12                 __________________________________________________________________________               Rate 125 g/ha                 Rate 62 g/ha                           __________________________________________________________________________     Barley Igri                                                                              30 35 35 40 35 0  10 10 25 -- 25 20 -- 20 20 25 15                                                                               15                 Barnyardgrass                                                                            20 70 45 80 45 50 40 40 50 -- 70 20 -- 10 60 15 30                                                                               15                 Blackgrass                                                                               15 55 25 60 20 30 50 50 50 -- 55 30 -- 25 30 30 30                                                                               20                 Chickweed 30 90 30 70 50 0  100                                                                               100                                                                               80 -- 65 95 -- 35 95 70 25                                                                               50                 Cocklebur 60 -- 50 85 75 20 30 40 30 -- 30 45 -- 15 55 50 45                                                                               20                 Corn      15 65 30 65 40 10 20 30 10 -- 60 20 -- 0  25 15 20                                                                               10                 Cotton    50 90 65 90 90 0  20 70 20 -- 70 70 -- -- 85 25 --                                                                               70                 Crabgrass 35 90 85 95 85 25 20 15 30 -- 90 25 -- 15 35 10 50                                                                               45                 Downy brome                                                                              25 20 0  40 10 0  0  0  20 -- 35 0  -- 0  0  0  20                                                                               0                  Duck salad                                                                               0  15 10 30 25 0  0  40 50 70 0  10 25 0  0  0  10                                                                               0                  Galium    40 30 25 55 40 0  10 0  -- 10 50 -- 20 20 60 30 0                    Giant foxtail                                                                            30 90 25 95 40 65 20 20 40 -- 95 20 -- 15 80 15 30                                                                               20                 It. rygrass                                                                              10 60 0  60 35 25 15 50 20 50 0  -- 0  35 20 0  0                    Johnsongrass                                                                             20 95 50 95 85 0  30 50 30 -- 95 45 -- 0  25 10 35                                                                               20                 Lambsquarter                                                                             10 -- 80 50 75 0  35 35 50 -- 15 80 -- 55 0  50 0 30                 Morningglory                                                                             30 90 65 90 85 20 35 50 50 -- 70 70 -- 40 80 20 55                                                                               65                 Rape      40 100                                                                               70 95 0  25 60 30 -- 90 70 -- 40 45 40 10 40                   Redroot pigweed                                                                          35 90 90 90 90 0  -- 80 90 -- 70 60 -- 25 80 80 70                                                                               75                 Rice japonica                                                                            10 40 40 50 65 10 15 25 65 10 40 10 10 0  0  0  20                                                                               10                 Soybean   20 50 65 65 60 0  20 35 50 -- 0  70 -- 30 35 -- --                                                                               --                 Speedwell 90 100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               -- -- 100                                                                               100                                                                               -- 90 100                                                                               0  35                                                                               85                 Sugar beet                                                                               45 100                                                                               100                                                                               90 95 0  80 100                                                                               30 -- 90 100                                                                               -- 0  95 -- 95                                                                               85                 Umbrella sedge                                                                           35 45 40 85 70 30 90 95 90 20 70 85 65 10 70 35 70                                                                               15                 Velvetleaf                                                                               40 95 65 95 85 0  20 50 20 -- 70 80 -- 15 80 35 65                                                                               60                 Watergrass 2                                                                             25 85 70 65 70 20 70 55 80 30 85 30 45 10 55 20 55                                                                               25                 Wheat     15 40 0  25 25 0  0  0  50 -- 25 25 -- 20 10 10 10                                                                               0                  Wild buckwheat                                                                           60 95 30 100                                                                               30 0  45 45 30 -- 30 35 -- 0  70 0  55                                                                               10                 Wild oat  25 50 30 75 55 20 35 50 50 -- 60 35 -- 0  30 40 25                                                                               20                 Barnyardgrass 2                                                                          20 80 65 70 55 25 85 85 85 25 75 35 50 25 50 35 40                   __________________________________________________________________________                                    COMPOUND                                                                       13 14 17 23 24 25 26 37 55 58 62                                               Rate 62 g/ha                                    __________________________________________________________________________                          Barley Igri                                                                              -- 10 20 30 30 35 25 0  0  10                                                                               25                                      Barnyardgrass                                                                            -- 20 15 70 25 70 40 10 20 15                                                                               25                                      Blackgrass                                                                               -- 20 10 35 0  50 10 20 25 20                                                                               30                                      Chickweed -- 30 20 80 10 70 45 0  95 100                                                                              60                                      Cocklebur -- 30 50 80 45 -- 70 10 25 40                                                                               10                                      Corn      -- 15 15 45 25 55 35 0  10 15                                                                               10                                      Cotton    -- 75 45 90 50 90 90 0  0  35                                                                               20                                      Crabgrass -- 25 25 90 85 95 80 10 10 10                                                                               20                                      Downy brome                                                                              -- 15 10 15 0  20 0  0  0  0 0                                       Duck salad                                                                               0  0  0  0  0  0  25 0  0  30                                                                               50                                      Galium    -- 10 20 25 25 55 25 0  10 10                                                                               0                                       Giant foxtail                                                                            -- 30 20 75 15 90 30 10 10 10                                                                               20                                      It. rygrass                                                                              -- 10 10 40 0  25 20 10 10 20                                                                               0                                       Johnsongrass                                                                             -- 20 10 90 40 90 80 0  20 15                                                                               --                                      Lambsquarter                                                                             -- 10 0  0  50 40 70 0  35 35                                                                               50                                      Morningglory                                                                             -- 30 30 85 0  85 85 0  30 35                                                                               35                                      Rape      -- 20 30 90 15 95 85 0  20 60                                                                               30                                      Redroot pigweed                                                                          -- 20 30 90 90 90 90 0  40 50                                                                               90                                      Rice japonica                                                                            20 0  25 30                                                                             40 10 0  10 15 55                                           Soybean   -- 0  10 50 50 65 60 0  10 20                                                                               35                                      Speedwell -- 75 75 100                                                                               90 -- 100                                                                               85 100                                                                               100                                                                              --                                      Sugar beet                                                                               -- 15 25 100                                                                               95 -- 95 0  80 100                                                                              30                                      Umbrella sedge                                                                           0  20 25 40 0  85 60 20 80 95                                                                               85                                      Velvetleaf                                                                               -- 45 40 90 20 90 75 0  10 30                                                                               0                                       Watergrass 2                                                                             0  40 0  0  40 65 45 15 35 35                                                                               70                                      Wheat     -- 0  10 25 0  20 20 0  0  0 50                                      Wild buckwheat                                                                           -- --30                                                                              70 15 90 30 0  45 10 20                                        Wild oat  -- 20 25 45 25 60 40 10 30 40                                                                               40                                      Barnyardgrass 2                                                                          0  35 0  70 45 60 50 10 35 55                                                                               75                 __________________________________________________________________________     PREEMERGENCE                                                                             COMPOUND          COMPOUND                                                     4  5  6  12 13 24 1  2  3  4  5  6  12 13 14 17  23                           Rate 500 g/ha      Rate 250 g/ha                                      __________________________________________________________________________     Barley Igri                                                                              0  55 20 25 0  45 70 30 35 0  35 10 0  0  10 10  30                  Barnyardgrass                                                                            40 80 50 55 40 90 95 75 100                                                                               20 70 20 30 20 80 30  100                 Blackgrass                                                                               60 95 90 90 75 100                                                                               90 65 95 20 90 90 80 30 75 55  100                 Chickweed 90 95 85 70 80 65 100                                                                               70 100                                                                               70 95 75 -- 80 85 100 100                 Cocklebur 0  0  10 0  0  0  0  0  0  0  0  0  0  0  0  20  0                   Corn      0  35 20 0  10 35 90 20 25 0  35 10 0  0  15 0   35                  Cotton    25 30 10 30 40 0  0  0  50 20 20 0  10 10 0  0   --                  Crabgrass 100                                                                               100                                                                               65 90 90 100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               50 85 -- 100                                                                               65  100                 Downy brome                                                                              10 10 10 0  10 30 95 20 35 0  10 10 0  0  35 35  95                  Galium    10 90 10 0  30 50 25 70 100                                                                               0  0  0  0  0  25 75  90                  Giant foxtail                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                 It. rygrass                                                                              30 80 35 25 25 95 100                                                                               30 70 15 60 0  10 25 30 35  100                 Johnsongrass                                                                             20 70 10 20 35 55 80 70 100                                                                               15 70 10 10 30 60 45  95                  Lambsquarter                                                                             95 100                                                                               95 100                                                                               95 95 100                                                                               60 95 95 60 80 95 25 90 95  100                 Morningglory                                                                             30 70 35 35 20 65 90 95 60 20 -- 25 30 15 40 50  95                  Rape      80 20 10 0  0  35 95 30 70 35 20 10 0  0  20 60  100                 Redroot pigweed                                                                          100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 95 90 95 30  100                 Soybean   0  0  0  0  10 20 10 10 20 0  0  0  0  0  20 --  0                   Speedwell -- 100                                                                               95 95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               -- 100                                                                               95 95 100                                                                               -- --  --                  Sugar beet                                                                               100                                                                               95 90 40 90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 -- 40 80 95 90  100                 Velvetleaf                                                                               40 75 45 60 25 70 100                                                                               100                                                                               90 40 60 30 40 20 30 20  85                  Wheat     10 55 20 20 10 20 65 20 65 0  30 10 10 10 20 30  45                  Wild buckwheat                                                                           35 95 0  75 40 40 90 35 25 20 95 0  60 40 70 80  100                 Wild oat  20 95 85 95 35 75 100                                                                               50 60 10 85 65 85 20 75 35  100                 __________________________________________________________________________               COMPOUND             COMPOUND                                                  24 25 26 37 55 58 62 1  2  3  4  5  6  7  12 13  14                            Rate 250 g/ha        Rate 125 g/ha                                   __________________________________________________________________________     Barley Igri                                                                              25 45 20 10 0  0  0  5  20 25 0  20 0  0  0  0   10                  Barnyardgrass                                                                            70 95 20 50 90 90 95 80 50 85 15 40 10 35 10 10  60                  Blackgrass                                                                               90 100                                                                               100                                                                               75 55 30 100                                                                               80 40 75 20 40 70 35 80 20  65                  Chickweed 60 100                                                                               100                                                                               100                                                                               95 95 65 85 60 90 50 45 -- 35 60 65                      Cocklebur 0  10 10 0  0  0  0  0  0  0  0  0  0  0  0  0   0                   Corn      0  60 10 35 10 0  0  75 20 10 0  15 0  30 0  0   0                   Cotton    0  20 0  0  0  0  25 0  0  10 10 0  0  0  10 0   0                   Crabgrass 95 100                                                                               100                                                                               100                                                                               95 50 100                                                                               95 90 100                                                                               95 85 35 95 35 65  80                  Downy brome                                                                              10 100                                                                               95 35 10 20 10 55 10 35 0  0  0  35 0  0   30                  Galium    30 100                                                                               0  65 10 10 10 25 45 80 0  0  0  10 0  0   20                  Giant foxtail                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               95 90 70 100                                                                               95 95  100                 It. rygrass                                                                              90 100                                                                               90 65 30 30 90 100                                                                               10 70 15 10 0  65 0  25  25                  Johnsongrass                                                                             25 90 50 30 20 20 50 45 30 60 0  30 0  55 0  10  40                  Lambsquarter                                                                             95 100                                                                               65 65 95 90 95 95 60 -- 95 0  20 90 0  --  50                  Morningglory                                                                             70 65 30 60 60 90 75 80 50 10 65 20 60 25 10 30                      Rape      35 100                                                                               35 10 65 55 35 65 20 45 20 10 0  10 0  0   20                  Redroot pigweed                                                                          95 100                                                                               100                                                                               50 100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               95 60 95 45 85 50  0                   Soybean   0  20 10 30 95 10 0  0  0  15 0  -- -- 10 0  --  20                  Speedwell 100                                                                               -- -- 100                                                                               100                                                                               95 100                                                                               100                                                                               95 100                                                                               -- 90 0  100                                                                               95 100                     Sugar beet                                                                               95 100                                                                               100                                                                               0  95 100                                                                               95 100                                                                               100                                                                               100                                                                               35 -- 30 95 20 30  95                  Velvetleaf                                                                               70 100                                                                               20 30 70 75 65 100                                                                               80 70 30 20 20 30 30 10  30                  Wheat     0  50 10 10 10 0  0  40 10 20 0  25 0  0  10 0                       Wild buckwheat                                                                           40 95 0  85 20 60 35 60 25 10 10 70 0  35 25 10  --                  Wild oat  45 100                                                                               65 45 30 20 90 100                                                                               25 40 0  35 30 35 65 10  60                  __________________________________________________________________________               COMPOUND                   COMPOUND                                            17 23 24 25 26 37 55 58 62 1  2  3  4  5  6  7  12 13                __________________________________________________________________________               Rate 125 g/ha              62 g/ha                                   __________________________________________________________________________     Barley Igri                                                                              0  25 0  0  0  10 10 0  35 10 25 0  10 0  0  0  0 0                  Barnyardgrass                                                                            25 65 35 70 10 35 40 40 90 80 30 50 10 40 10 10 0 10                 Blackgrass                                                                               45 -- 65 95 55 70 30 30 50 80 30 20 -- 40 20 30 80                                                                               20                 Chickweed 80 100                                                                               55 100                                                                               100                                                                               20 90 95 65 55 30 90 50 45 30 0  60                                                                               40                 Cocklebur 0  0  0  0  0  0  0  0  0  0  0  0  0  0  0  0  0 0                  Corn      0  35 0  45 0  15 10 0  0  65 10 0  0  -- 0  0  0 0                  Cotton    0  0  0  20 0  0  0  0  20 0  0  0  0  0  0  0  0 0                  Crabgrass -- 100                                                                               95 100                                                                               -- 60 90 -- 100                                                                               95 70 100                                                                               70 45 35 -- 25                                                                               60                 Downy brome                                                                              20 25 0  85 25 0  10 20 0  30 0  35 0  0  0  10 0 0                  Galium    30 0  10 100                                                                               0  0  0  10 0  25 35 10 0  0  0  0  0 0                  Giant foxtail                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               85 95 95 100                                                                               100                                                                               95 100                                                                               90 90 20 95 55                                                                               50                 It. rygrass                                                                              30 0  60 85 20 30 20 30 40 95 0  65 0  0  0  20 0 25                 Johnsongrass                                                                             40 70 10 75 20 20 10 20 30 35 10 60 0  25 0  35 0 10                 Lambsquarter                                                                             90 100                                                                               90 100                                                                               65 35 70 90 80 95 60 80 0  0  0  85 0 20                 Morningglory                                                                             35 -- 35 70 35 10 30 60 65 65 50 50 10 35 10 50 15                                                                               10                 Rape      35 30 0  80 20 0  30 55 20 65 10 0  0  0  0  0  0 0                  Redroot pigwee 30                                                                        100                                                                               85 100                                                                               100                                                                               0  100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               50 -- 85 40 70 25                   Soybean   20 0  0  20 0  30 20 0  0  0  0  0  0  0  0  10 0 0                  Speedwell -- -- 100                                                                               -- -- 100                                                                               100                                                                               95 90 100                                                                               90 100                                                                               -- 90 0  20 30                                                                               100                Sugar beet                                                                               85 100                                                                               95 95 100                                                                               0  95 100                                                                               85 100                                                                               70 65 15 95 10 90 20                                                                               0                  Velvetleaf                                                                               20 75 35 85 0  0  30 70 35 70 60 50 20 20 0  30 15                                                                               --                 Wheat     20 25 0  25 0  10 0  0  0  35 0  -- 0  20 0  0  10                                                                               0                  Wild buckwheat                                                                           70 85 10 90 0  20 20 60 15 60 20 0  0  70 0  0  0 0                  Wild oat  30 65 35 85 35 35 20 10 30 95 0  30 0  30 30 25 40                                                                               10                 __________________________________________________________________________                                       COMPOUND                                                                          14 17 23 24 25 26 37                                                                               55                                                                               58                                                                               62                __________________________________________________________________________                                 Barley Igri                                                                             0  0  15 0  0  0  0 0 0 0                                             Barnyardgrass                                                                           25 25 30 25 55 10 10                                                                               25                                                                               30                                                                               40                                            Blackgrass                                                                              30 35 100                                                                               45 95 55 35                                                                               20                                                                               25                                                                               30                                            Chickweed                                                                               70 80 100                                                                               20 100                                                                               95 0 20                                                                               --                                                                               40                                            Cocklebur                                                                               0  0  0  0  0  0  0 0 0 0                                             Corn     0  0  10 0  30 0  0 0 0 0                                             Cotton   0  0  0  0  20 0  0 0 0 0                                             Crabgrass                                                                               30 40 100                                                                               50 95 100                                                                               40                                                                               40                                                                               50                                                                               90                                            Downy brome                                                                             10 0  10 0  60 0  0 0 10                                                                               0                                             Galium   10 25 0  0  40 0  0 0 0 0                                             Giant foxtail                                                                           100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               85                                                                               85                                                                               35                                                                               100                                           It. rygrass                                                                             15 20 0  20 20 0  20                                                                               85                                                                               35                                                                               100                                           Johnsongrass                                                                            40 20 35 0  25 20 10                                                                               0 10                                                                               20                                            Lambsquarter                                                                            20 20 85 45 100                                                                               65 30                                                                               70                                                                               60                                                                               70                                            Morningglory                                                                            30 20 60 35 45 20 10                                                                               30                                                                               30                                                                               40                                            Rape     10 20 20 0  40 0  0 20                                                                               20                                                                               0                                             Redroot pigweed                                                                         0  30 100                                                                               -- 100                                                                               100                                                                               0 90                                                                               95                                                                               90                                            Soybean  0  0  0  0  20 0  0 10                                                                               0 0                                             Speedwell                                                                               -- -- -- 100                                                                               -- -- 100                                                                              70                                                                               --                                                                               75                                            Sugar beet                                                                              70 65 100                                                                               80 95 100                                                                               0 65                                                                               70                                                                               --                                            Velvetleaf                                                                              0  0  15 30 65 0  0 10                                                                               10                                                                               25                                            Wheat    0  0  0  0  10 0  0 0 0 0                                             Wild buckwheat                                                                          0  70 80 0  90 0  0 10                                                                               25                                                                               10                                            Wild oat 35 25 45 10 65 0  0 10                                                                               10                                                                               20                __________________________________________________________________________

                                      TABLE C                                      __________________________________________________________________________     POSTEMERGENCE                                                                           COMPOUND                                                              Rate 31 g/ha                                                                            1  2 3  7 14                                                                               17                                                                               23 25 26 37                                                                               55                                                                               58 62                                      __________________________________________________________________________     Barley Igri                                                                             20 20                                                                               -- 10                                                                               0 20                                                                               30 25 20 0 0 10 20                                      Barnyardgrass                                                                           50 10                                                                               -- 30                                                                               10                                                                               10                                                                               45 50 40 10                                                                               10                                                                               10 20                                      Blackgrass                                                                              30 10                                                                               -- 20                                                                               10                                                                               10                                                                               25 20 10 0 25                                                                               20 30                                      Chickweed                                                                               50 80                                                                               -- 20                                                                               30                                                                               20                                                                               75 55 30 0 95                                                                               100                                                                               40                                      Cocklebur                                                                               20 40                                                                               -- 40                                                                               10                                                                               40                                                                               70 85 70 0 15                                                                               40 10                                      Corn     30 20                                                                               -- 15                                                                               10                                                                               10                                                                               35 50 35 0 0 10 0                                       Cotton   40 55                                                                               -- 45                                                                               30                                                                               30                                                                               90 90 90 0 0 25 10                                      Crabgrass                                                                               35 20                                                                               -- 50                                                                               20                                                                               20                                                                               90 85 80 10                                                                               10                                                                               10 10                                      Downy brome                                                                             10 0 -- 0 10                                                                               0 10 15 0  0 0 0  0                                       Duck salad                                                                              0  0 10 0 0 0 0  0  0  0 0 0  35                                      Galium   0  45                                                                               -- 25                                                                               10                                                                               --                                                                               20 50 25 0 10                                                                               10 0                                       Giant foxtail                                                                           60 10                                                                               -- 30                                                                               25                                                                               10                                                                               70 85 30 0 10                                                                               10 20                                      It. rygrass                                                                             40 0 -- 0 0 0 30 20 0  0 0 10 0                                       Johnsongrass                                                                            80 30                                                                               -- 20                                                                               10                                                                               0 85 85 65 0 10                                                                               0  --                                      Lambsquarter                                                                            0  80                                                                               -- 0 0 0 0  35 70 0 30                                                                               30 20                                      Morningglory                                                                            70 --                                                                               -- --                                                                               10                                                                               20                                                                               80 80 80 0 20                                                                               30 30                                      Rape     85 30                                                                               -- 10                                                                               20                                                                               15                                                                               70 90 75 0 20                                                                               60 0                                       Redroot pigweed                                                                         65 60                                                                               -- 70                                                                               10                                                                               30                                                                               90 90 90 0 40                                                                               50 80                                      Rice japonica                                                                           20 10                                                                               10 20                                                                               0 0 0  25 0  0 0 0  35                                      Soybean  0  60                                                                               -- 40                                                                               0 10                                                                               25 65 60 0 0 -- 20                                      Speedwell                                                                               100                                                                               95                                                                               -- 20                                                                               60                                                                               20                                                                               95 100                                                                               100                                                                               85                                                                               95                                                                               100                                                                               --                                      Sugar beet                                                                              90 80                                                                               -- 70                                                                               10                                                                               20                                                                               45 90 90 0 55                                                                               100                                                                               25                                      Umbrella sedge                                                                          65 55                                                                               35 60                                                                               20                                                                               0 30 75 60 0 70                                                                               75 75                                      Velvetleaf                                                                              60 80                                                                               -- 50                                                                               30                                                                               30                                                                               85 90 70 0 10                                                                               20 0                                       Watergrass 2                                                                            70 20                                                                               10 30                                                                               30                                                                               0 65 50 45 0 10                                                                               25 60                                      Wheat    25 10                                                                               -- 0 0 10                                                                               25 10 10 0 0 0  20                                      Wild buckwheat                                                                          20 30                                                                               -- 30                                                                               40                                                                               20                                                                               60 80 30 0 0 10 0                                       Wild oat 40 25                                                                               -- 25                                                                               15                                                                               20                                                                               40 45 20 10                                                                               30                                                                               30 30                                      Barnyardgrass 2                                                                         65 30                                                                               30 20                                                                               25                                                                               0 45 55 40 0 10                                                                               30 70                                      __________________________________________________________________________     PREEMERGENCE                                                                   COMPOUND                                                                       Rate 31 g/ha                                                                            1  2 3  7 14                                                                               17                                                                               23 25 26 37                                                                               55                                                                               58 62                                      __________________________________________________________________________     Barley Igri                                                                             10 0 20 0 0 0 0  0  0  0 0 0  0                                       Barnyardgrass                                                                           70 10                                                                               40 10                                                                               0 0 15 25 0  0 10                                                                               20 10                                      Blackgrass                                                                              45 25                                                                               20 10                                                                               20                                                                               35                                                                               55 55 20 10                                                                               10                                                                               25 20                                      Chickweed                                                                               30 10                                                                               70 0 35                                                                               70                                                                               100                                                                               100                                                                               90 0 10                                                                               90 40                                      Cocklebur                                                                               0  0 0  0 0 0 0  0  0  0 0 0  0                                       Corn     50 10                                                                               0  0 0 0 10 0  0  0 0 0  0                                       Cotton   0  0 0  0 0 0 0  0  0  0 0 0  0                                       Crabgrass                                                                               95 30                                                                               70 85                                                                               25                                                                               40                                                                               100                                                                               90 45 30                                                                               30                                                                               30 35                                      Downy brome                                                                             20 0 25 0 0 0 0  40 0  0 0 0  0                                       Galium   10 10                                                                               10 0 10                                                                               0 0  25 0  0 0 0  0                                       Giant foxtail                                                                           100                                                                               90                                                                               95 90                                                                               80                                                                               80                                                                               100                                                                               100                                                                               55 40                                                                               60                                                                               -- 100                                     It. rygrass                                                                             90 0 0  20                                                                               10                                                                               0 0  0  0  0 0 10 10                                      Johnsongrass                                                                            30 0 10 35                                                                               0 0 10 10 0  0 0 10 0                                       Lambsquarter                                                                            90 30                                                                               80 35                                                                               10                                                                               0 0  90 0  20                                                                               10                                                                               45 60                                      Morningglory                                                                            60 --                                                                               20 30                                                                               0 20                                                                               -- 10 0  0 30                                                                               30 20                                      Rape     20 0 0  0 10                                                                               0 10 40 0  0 20                                                                               20 0                                       Redroot pigweed                                                                         100                                                                               75                                                                               100                                                                               35                                                                               0 30                                                                               100                                                                               100                                                                               70 0 70                                                                               95 90                                      Soybean  0  0 0  0 0 0 0  20 0  0 0 0  0                                       Speedwell                                                                               100                                                                               35                                                                               95 20                                                                               --                                                                               --                                                                               -- -- -- 95                                                                               10                                                                               95 --                                      Sugar beet                                                                              100                                                                               40                                                                               65 75                                                                               25                                                                               20                                                                               90 95 90 0 30                                                                               70 30                                      Velvetleaf                                                                              60 25                                                                               0  20                                                                               0 0 0  25 0  0 10                                                                               10 20                                      Wheat    30 0 0  0 0 0 0  0  0  0 0 0  0                                       Wild buckwheat                                                                          35 10                                                                               0  0 0 0 65 85 0  0 0 25 0                                       Wild oat 85 0 20 0 15                                                                               10                                                                               25 40 0  0 0 0  20                                      Wheat    30 0 0  0 0 0 0  0  0  0 0 0  0                                       Wild buckwheat                                                                          35 10                                                                               0  0 0 0 65 85 0  0 0 25 0                                       Wild oat 85 0 20 0 15                                                                               10                                                                               25 40 0  0 0 0  20                                      __________________________________________________________________________

                  TABLE C                                                          ______________________________________                                         POSTEMERGENCE                                                                                    COMPOUND                                                     Rate 16 g/ha        7     25                                                   ______________________________________                                         Barley Igri         10    20                                                   Barnyardgrass       20    50                                                   Blackgrass          15    20                                                   Chickweed           10    40                                                   Cocklebur           35    85                                                   Corn                15    50                                                   Cotton              40    90                                                   Crabgrass           15    85                                                   Downy brome         0     10                                                   Duck salad          0     0                                                    Galium              0     40                                                   Giant foxtail       20    85                                                   It. rygrass         0     10                                                   Johnsongrass        0     85                                                   Lambsquarter        0     30                                                   Morningglory        25    75                                                   Rape                10    75                                                   Redroot pigweed     35    90                                                   Rice japonica       10    20                                                   Soybean             30    65                                                   Speedwell           20    100                                                  Sugar beet          70    80                                                   Umbrella sedge      20    60                                                   Velvetleaf          25    90                                                   Watergrass 2        0     45                                                   Wheat               0     0                                                    Wild buckwheat      15    65                                                   Wild oat            20    40                                                   Barnyardgrass 2     0     50                                                   ______________________________________                                         PREEMERGENCE                                                                                     COMPOUND                                                     Rate 16 g/ha        7     25                                                   ______________________________________                                         Barley Igri         0     0                                                    Barnyardgrass       0     0                                                    Blackgrass          10    30                                                   Chickweed           0     100                                                  Cocklebur           0     0                                                    Corn                0     0                                                    Cotton              0     0                                                    Crabgrass           10    90                                                   Downy brome         0     0                                                    Galium              0     15                                                   Giant foxtail       80    95                                                   It. rygrass         0     0                                                    Johnsongrass        20    0                                                    Lambsquarter        10    85                                                   Morningglory        20    10                                                   Rape                0     10                                                   Redroot pigweed     20    100                                                  Soybean             0     20                                                   Speedwell           20    --                                                   Sugar beet          70    80                                                   Velvetleaf          10    10                                                   Wheat               0     0                                                    Wild buckwheat      0     40                                                   Wild oat            0     20                                                   ______________________________________                                    

TEST D

Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium pensylvanicum), common ragweed (Ambrosia artemisiifolia), corn (Zea mays), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), signalgrass (Brachiaria platyphylla), smartweed (Polygonum pensylvanicum), soybean (Glycine max), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a matapeake sandy loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one to four leaf stage), then treated postemergence with the test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. Pots receiving preemergence treatments were planted immediately prior to test chemical application. Pots treated in this fashion were placed in the greenhouse and maintained according to routine greenhouse procedures.

Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table D, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control.

                                      TABLE D                                      __________________________________________________________________________     PREEMERGENCE                                                                            COMPOUND 1                                                                              COMPOUND 1                                                                              COMPOUND 1                                                                              COMPOUND 1                                                                              COMPOUND 1                                                                              COMPOUND 1                        Rate 560 g/ha                                                                           Rate 280 g/ha                                                                           Rate 140 g/ha                                                                           Rate 70 g/ha                                                                            Rate 35 g/ha                                                                            Rate 17                  __________________________________________________________________________                                                           g/ha                     Barnyardgrass                                                                           100      100      75       60       25       10                       Bindweed 100      100      95       15       0        0                        Blk Nightshade                                                                          100      95       60       35       0        0                        Cassia   0        0        0        0        0        0                        Cocklebur                                                                               --       0        0        0        0        0                        Corn     95       85       75       50       15       10                       Cotton   0        10       0        0        0        0                        Crabgrass                                                                               100      100      100      100      55       15                       Fall panicum                                                                            100      100      95       80       25       15                       Giant foxtail                                                                           100      100      100      100      100      30                       Green foxtail                                                                           100      100      100      100      100      25                       Jimsonweed                                                                              60       0        0        0        0        0                        Johnsongrass                                                                            100      100      65       45       15       10                       Lambsquarter                                                                            100      95       55       15       0        0                        Morningglory                                                                            60       35       15       15       10       10                       Nutsedge 70       35       10       0        0        0                        Pigweed  100      100      100      100      85       0                        Prickly sida                                                                            50       40       10       0        0        0                        Ragweed  100      80       50       10       0        0                        Shattercane                                                                             80       65       45       15       0        0                        Signalgrass                                                                             100      100      100      95       70       25                       Smartweed                                                                               100      100      65       30       0        0                        Soybean  10       10       0        0        0        0                        Sunflower                                                                               15       10       0        0        0        0                        Velvetleaf                                                                              100      65       25       10       0        0                        Wild proso                                                                              100      80       40       30       0        0                        Woolly cupgrass                                                                         95       75       25       20       0        0                        Yellow foxtail                                                                          100      100      100      100      65       20                       __________________________________________________________________________     POSTEMERGENCE                                                                           COMPOUND 1  COMPOUND 1                                                                              COMPOUND 1  COMPOUND 1                                                                              COMPOUND 1                           Rate 280 g/ha                                                                              Rate 140 g/ha                                                                           Rate 70 g/ha                                                                               Rate 35 g/ha                                                                            Rate 17                     __________________________________________________________________________                                                        g/ha                        Barnyardgrass                                                                           65          55       50          20       0                           Bindweed 0           0        0           0        0                           Blk Nightshade                                                                          20          0        0           0        0                           Cassia   0           0        0           0        0                           Cocklebur                                                                               35          30       25          20       0                           Corn     50          40       35          20       15                          Cotton   85          85       80          65       60                          Crabgrass                                                                               60          55       45          0        0                           Fall panicum                                                                            75          70       65          0        0                           Giant foxtail                                                                           65          60       50          0        0                           Green foxtail                                                                           65          60       55          0        0                           Jimsonweed                                                                              55          50       50          40       40                          Johnsongrass                                                                            40          35       20          0        0                           Lambsquarter                                                                            45          40       25          35       25                          Morningglory                                                                            25          15       10          0        0                           Nutsedge 0           0        0           0        0                           Pigweed  60          55       45          40       35                          Prickly sida                                                                            0           0        0           0        0                           Ragweed  40          35       35          30       35                          Shattercane                                                                             20          15       15          5        0                           Signalgrass                                                                             25          20       15          0        0                           Soybean  50          35       25          0        0                           Sunflower                                                                               55          55       45          35       25                          Velvetleaf                                                                              75          65       60          50       35                          Wild proso                                                                              15          10       0           0        0                           Woolly cupgrass                                                                         20          20       15          0        0                           Yellow foxtail                                                                          60          60       55          0        0                           __________________________________________________________________________

TEST E

Compounds evaluated in this test were formulated in a non-phytoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test.

Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeum vulgare cv. `Igri`), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), downy brome (Bromus tectorum), galium (Galium aparine), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), speedwell (Veronica persica), ryegrass (Lolium multiflorum), spring wheat (Triticum aestivum cv. `ERA`), windgrass (Apera spica-venti), winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis) and wild oat (Avena fatua).

Blackgrass, galium and wild oat were treated at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table E, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (--) means no test result.

                                      TABLE E                                      __________________________________________________________________________     POSTEMERGENCE                                                                                                               COM-  COM-  COM-                           COMPOUND COMPOUND COMPOUND COMPOUND POUND 1                                                                              POUND                                                                                POUND 1                        1  23 25 1  23 25 1  23 25 1  23 25 Rate 31                                                                              Rate                                                                                 Rate 8                         Rate 500 g/ha                                                                           Rate 250 g/ha                                                                           Rate 125 g/ha                                                                           Rate 62 g/ha                                                                            g/ha  g/ha  g/ha                  __________________________________________________________________________     Blackgrass (2)                                                                          60 70 50 10 40 50 50 10 30 10 10 10 5     5     5                     Chickweed                                                                               100                                                                               100                                                                               100                                                                               80 70 100                                                                               60 65 80 50 50 50 45    5     5                     Downy brome                                                                             30 15 50 20 15 45 5  5  10 5  0  5  5     0     0                     Galium (2)                                                                              90 55 70 65 40 65 50 40 60 50 30 60 40    10    10                    Green foxtail                                                                           100                                                                               85 100                                                                               80 60 70 40 10 50 10 0  5  5     0     0                     Kochia   98 90 85 95 85 85 60 85 80 60 70 80 50    0     0                     Lambsquarters                                                                           100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               85 80 50 80 50 40 60 50    0     0                     Ryegrass 50 10 15 40 10 10 10 5  5  5  0  5  0     0     0                     Speedwell                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               60    60    40                    Wheat (Spring)                                                                          40 30 40 30 30 30 25 15 30 10 10 15 10    5     0                     Wheat (Winter)                                                                          30 30 30 20 25 10 20 10 10 10 10 5  10    5     5                     Wild buckwheat                                                                          100                                                                               100                                                                               100                                                                               98 100                                                                               90 70 70 80 5  60 55 5     0     0                     Wild mustard                                                                            100                                                                               100                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               70 60 100                                                                               40 55 10    10    5                     Wild oat (2)                                                                            50 35 45 40 35 30 20 30 30 10 10 10 10    10    5                     Windgrass                                                                               100                                                                               80 70 90 60 60 30 10 40 5  10 40 5     5     5                     Winter Barley                                                                           40 30 30 25 15 30 15 10 25 10 10 15 5     5     5                     __________________________________________________________________________     PREEMERGENCE                                                                                                                COM-  COM-  COM-                           COMPOUND COMPOUND COMPOUND COMPOUND POUND 1                                                                              POUND                                                                                POUND 1                        1  23 25 1  23 25 1  23 25 1  23 25 Rate 31                                                                              Rate                                                                                 Rate 8                         Rate 500 g/ha                                                                           Rate 250 g/ha                                                                           Rate 125 g/ha                                                                           Rate 62 g/ha                                                                            g/ha  g/ha  g/ha                  __________________________________________________________________________     Blackgrass (2)                                                                          100                                                                               100                                                                               100                                                                               70 60 40 60 50 10 40 5  5  5     0     0                     Chickweed                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               55 100                                                                               50 30 70 0     0     0                     Downy brome                                                                             100                                                                               100                                                                               -- 100                                                                               100                                                                               100                                                                               50 5  60 5  0  20 0     0     0                     Galium (2)                                                                              100                                                                               100                                                                               100                                                                               100                                                                               50 100                                                                               -- 50 50 100                                                                               -- 50 0     0     0                     Green foxtail                                                                           100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100   100   50                    Kochia   98 90 90 98 90 90 95 90 90 85 90 90 80    0     0                     Lambsquarters                                                                           90 95 95 90 95 95 90 80 90 90 0  70 0     0     0                     Ryegrass 100                                                                               80 100                                                                               100                                                                               80 10 60 10 5  50 0  0  5     0     0                     Speedwell                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               70 100                                                                               70    70    55                    Wheat (Spring)                                                                          60 40 50 40 25 50 35 5  20 10 5  5  5     0     0                     Wheat (Winter)                                                                          60 40 45 55 20 20 50 5  5  40 0  0  0     0     0                     Wild buckwheat                                                                          100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               80 90 70 50 70 0     0     0                     Wild mustard                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               40 40 60    5     0                     Wild oat (2)                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               80 80 80 80 40 55 10    5     0                     Windgrass                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               --    --    70                    Winter Barley                                                                           45 20 15 45 10 5  30 5  0  10 5  0  0     0     0                     __________________________________________________________________________ 

I claim:
 1. A compound of Formula I: ##STR18## X is a single bond; O, S; or NR⁴ ; Y is O; S; or NCH₃ ;Z is CH or N; W is CH or N; R¹ is C₁ -C₅ alkyl optionally substituted with C₁ -C₂ alkoxy, OH, 1-3 halogens, or C₁ -C₂ alkylthio; CH₂ (C₃ -C₄ cycloalkyl); C₃ -C₄ cycloalkyl optionally substituted with 1-3 methyl groups; C₂ -C₄ alkenyl; C₂ -C₄ haloalkenyl; or phenyl; R² is H; chlorine: bromine; C₁ -C₂ alkyl; C₁ -C₂ alkoxy; C₁ -C₂ alkylthio; C₂ -C₃ alkoxyalkyl; C₂ -C₃ alkylthioalkyl; cyano; nitro; NH(C₁ -C₂ alkyl); or N(C₁ -C₂ alkyl)₂ ; R³ is C₁ -C₄ haloalkyl; C₁ -C4 haloalkoxy; C₁ -C₄ haloalkylthio; halogen; cyano; nitro; or methylthio; R⁴ is H; CH₃ or OCH₃ ; and agriculturally suitable salts thereof.
 2. A compound of claim 1 wherein:R¹ is C₁ -C₄ alkyl optionally substituted with methoxy or 1-3 halogens; C₂ -C₄ alkenyl; or C₂ -C₄ haloalkenyl; R² is chlorine; bromine; C₁ -C₂ alkyl; C₁ -C₂ alkoxy; cyano; nitro; NH(C₁ -C₂ alkyl); or N(C₁ -C₂ alkyl)₂.
 3. A compound of claim 2 wherein:X is a single bond; R³ is C₁ -C₂ haloalkyl; C₁ -C₂ haloalkoxy; C₁ -C₂ haloalkylthio; chlorine or bromine.
 4. A compound of claim 3 wherein:Q is Q-1 or Q-2.
 5. A compound according to claim 4 which is:2-methyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyridinyl]phenyl]-propanamide; or 2-methyl-N-[4-methyl-2-[2-(trifluoromethylthio)-4-pyrimidinyl]-phenyl]propanamide.
 6. A composition for controlling growth of undesired vegetation comprising an effective amount of a compound of claim 1 and at least one of a surfactant, solid or liquid diluent.
 7. A composition for controlling growth of undesired vegetation comprising an effective amount of a compound of claim 2 and at least one of a surfactant, solid or liquid diluent.
 8. A composition for controlling growth of undesired vegetation comprising an effective amount of a compound of claim 4 and at least one of a surfactant, solid or liquid diluent.
 9. A composition for controlling growth of undesired vegetation comprising an effective amount of a compound of claim 5 and at least one of a surfactant, solid or liquid diluent.
 10. A method for controlling growth of undesired vegetation comprising applying to the locus to be protected an effective amount of the composition of claim
 6. 